Enantion Selective Synthesis of Chairal Alfa Amino Acids by Phase Transfer Catalysts

Introduction

Amino Acids are as base the units of lipids & proteins formations which they are used to make medicine. Relocating Amino acids molecules on chemical’s protein chains will produces new productions with new properties. Also, due to cell’s receptor in form of chiral, each Amino Acids enantiomers lead to new medicine or cause their effects. Therefore, producing new different Amino Acids enantiomers will design for new medicine. So, according to above information we have concluded the importance of the Amino Acids generation in chemical labs as for the medicine uses.

There are different types of Amino Acids. Except Amino Acid Glycine، Each Amino Acid made of an asymmetric Carbon called α- carbon  which is banded in four different  groups  as  Carboxyl (COOH) -Base Amine (NH2),  a R- side chain and a Hydrogen band . most Amino Acids are participating in Synthesis Protein’s products. While the β-Amino Acids & γ and δ are intermediate chemical interaction.  Most Amino Acids in PH level 7 are in shape of two       poles means NH₂⁺ and the other group COOH loosing the Hydrogen and show as COO⁻. Now if the NH2 agent respect to Alpha Amino Acid chain (in space figure) connect to Left side, it marked  as  (L) Amino Acid otherwise if the NH2 connect to right side of chain marked as (R).

Alpha Amino Acids is one of the important compounds in medicine productions industry. due to their strong and stable chemical transactions , and yet,  easy  biological accessibility,  their synthesis production are the industries attention. Recently Scott & Ednel reported; they have synthesis Alpha Amino Acid from Acids and lipids solid phase state. they used “De Phenyl Imine Glycine Esther to synthesis the Alpha Amino Acid. As it known, they are different Amino Acids for different lipids, peptides and proteins base unites. So, as these fact each Amino Acids could leads to new/different medicine productions. It is another reasons synthesis Amino Acids is getting highly industries attention. It should pay attention, in plan to design and produce medicines, our body’s cell’s respirators are Chiral. Therefore used Amino Acids arrangement could produce different types of medicines with different effects.  The goal of this research is also to covert the Amino Acids Glycine (Carbonless Chiral) to desirable Amino Acids with C- alkylation reaction in proper salty chemical environmental in present of glycine as catalyst. Also the Alkyl agent & a Catalyst in organic Phase and forming mono Anion it’s the mono alkylation Glycine synthesis result. This research’s renovation is controlling the amount of Base which react with Amino Acid and lead to forming Mono Anion and the mono mono alkylation Glycine chiral result. Notice; by using an organic Base LDA (Lithium Di Isopropyl) presenting in organic Phase at the same time, forming Di Alkyl Glycine is possible.

Experimental details

General method

All of reagents used in this research work were GR grade and all of solvents were distilled before use. Japanese weighing with 0.100 g sensivity model ANDGF-300, hitter and stirrer model Heidolphm Rn3004 Safty, Merk thin layer chromatography sheets Art no: 1:0554, Electrothermal melting point measurement apparatus , Memmert (oven) materials and glossy instruments desicator (oven), The structure elucidation was determined utilizing JEOL DELTA NMR 400 MHz (1H-NMR) and 100 MHz (13C-NMR) using CDCl3 and DMSO as solvent, and IR spectra were recorded on Perkin-Elmer-1420 Spectrophotometer. Spectrophotometer with using CDCl3 and DMSO as solvent, at University Shahr rey branch, and University of Tehran Iran.

Synthesis Methods

Methyl glycine family separately were synthesized and consequently, many new kind of imino ester glycine were obtained from these compounds.

General procedure for the Preparation of imino ester glycine

4 g (0/031mol) methyl glycine hydrochloride as the raw material used and the 3/370 g (0/031mol) benzaldehyde and 10 ml tree ethyl amine added and then 60 ml CH₂Cl₂ of the solvent used in this series 3 g Na₂So₄ Moreover, as a sorbent Add all the ingredients mixed together and 1 hour to make ends followed by Buchner magnesium sulfate eliminates hopper remove the funnel solution and by rotary solvent methylene chloride to remove then the organic phase Na₂SO₄ for dewatering Add funnel and chemical imino ester glycine was obtained.

To give (0.32 g, 90%); A white crystal; Mp: 205; IR (KBr): 3028, 2862, 1747, 1646, 644;  ¹ H-NMR (400 MHz, CDCl₃) ä  3.65 (s, 3H), 4.51 (d, 2H), 7.29 (d, 3H), 7.62 – 7.62  (J =2 and 8 Hz, t, 2H), 8.12 (s, 1H); ¹³ C NMR (CDCL₃) δ 51.6, 58.5, 128.8, 129.6, 139.7, 161.0, 170.3; MS m/z 177 (M⁺, 85.01); Anal.Calcd for C₁₀H₁₁NO₂: C, 67.78; H, 6.26; N, 7.90;            O, 18.60. Found: C, 67.98; H, 6.10; N, 7.85; O, 18.75.

Synthesis of imino ester glycine derivatives structure

Compound 1: To give (0.35 g, 95%); A white crystal; Mp: 108; IR (KBr): 3020, 2875, 1745, 1652, 710; ¹ H-NMR (400 MHz, CDCl₃) ä 1.46 (d, 3H),  3.67 (s, 3H), 4.14 (m, 1H), 7.29  (J =2 and 8 Hz, d, 3H), 7.62 – 7.64 (t, 2H), 8.11 (s, 1H); ¹³ C NMR (CDCL₃) δ 18.0, 51.9, 66.6, 128.9, 129.2, 131.1, 139.9, 160.9, 171.4; MS m/z 191 (M⁺, 92.16); Anal.Calcd for C₁₁H₁₃NO₂: C, 69.09;  H, 6.85; N, 7.32; O, 16.73. Found: C, 67.98; H, 6.69; N, 7.08; O, 16.20.

Compound 2: To give (0.32 g, 85%); A White crystal; Mp: 181; IR (KBr): 3125, 2935, 1745, 1595, 659; ¹ H-NMR (400 MHz, CDCl₃) ä 2.7 (t, 3H), 2.8 – 3.1 (m, 2H), 3.67 (s, 3H), 7.08 (m, 1H), 7.12 (m, 2H), 7.21- 7.24 (m, 2H), 7.30- 7.32 (J =2 and 8 Hz, q, 5H), 7.50 (d, 1H); ¹³ C NMR (CDCL₃) δ 34.00, 42.3, 51.9, 122.3, 127.3, 127.8, 128.7, 130.1, 139.5, 149.2, 163.4, 170.01; MS m/z 267 (M⁺, 90.01); Anal.Calcd for C₁₇H₁₇NO₂: C, 76.38; H, 6.41; N, 5.24;  O, 11.97. Found: C, 75.98; H, 6.52; N, 5.32; O, 12.10.

Compound 3: To give (0.40 g, 99%); A brown crystal; Mp: 217; IR (KBr): 3025, 2920, 1732, 1610, 700; ¹ H-NMR (400 MHz, CDCl₃) ä 2.55- 2.80 (m, 2H), 3.67 (s, 3H), 4.01- 4.06 (d, 2H), 4.97- 5.03(m, 1H), 5.70 (q, 1H), 7.29 (d, 3H), 7.62 (t, 2H), 8.09- 8.11 (J =2 and 8 Hz, s, 1H);     ¹³ C NMR (CDCL₃) δ 38.9, 51.9, 70.6, 116.4, 128.9, 129.2, 131.1, 134.4, 139.9, 1160.9, 171.4; MS m/z 217 (M⁺, 85.20); Anal.Calcd for C₁₃H₁₅NO₂: C, 71.87; H, 6.96; N, 6.45; O, 14.73. Found: C, 71.98; H, 6.54; N, 6.50; O, 14.20.

Compound 4: To give (0.30 g, 80.3%); A Yellow crystal; Mp: 191; IR (KBr): 3028, 2835, 1740, 1635, 710; ¹ H-NMR (400 MHz, CDCl₃) ä 0.96 (t, 3H), 2.04 (m, 2H), 3.67 (s, 3H), 3.96 (t, 1H), 7.29- 7.31 (J =2 and 8 Hz, d, 3H), 7.62 (t, 2H), 8.13 (s, 1H); ¹³ C NMR (CDCL₃) δ 18.9, 23.9, 51.9, 71.7, 128.9, 129.2, 131.1, 139.9, 160.9, 171.4; MS m/z 205 (M⁺, 78.96); Anal.Calcd for C₁₀H₂₁NO₂: C, 70.22; H, 7.37; N, 6.82; O, 15.59. Found: C, 70.10; H, 7.89; N, 6.24; O, 15.10.

Compound 5: To give (0.38 g, 98%); A yellow crystal; Mp: 244; IR (KBr): 3025, 2870, 1735, 1642, 725; ¹ H-NMR (400 MHz, CDCl₃) ä 3.67 (s, 3H), 5.23- 5.25 (J =2 and 8 Hz, d, 1H),    7.28- 7.29 (d, 3H), 7.62- 7.64 (t, 2H), 8.11 (s, 1H), 8.60 (d, 2H); ¹³ C NMR (CDCL₃) δ 51.9, 68.5, 124.3, 128.9, 129.2, 131.1, 139.9, 146.5, 149.9, 160.9, 171; MS m/z 254 (M⁺, 99.05); Anal.Calcd for C₁₅H₁₄N₂O₂: C, 70.85; H, 5.55; N, 11.02; O, 12.58. Found: C, 70.54; H, 5.98;    N, 10.97; O, 12.10.

Compound 6: To give (0.31 g, 89%); A yellow crystal; Mp: 250; IR (KBr): 3125, 2970, 1725, 1632, 715; ¹ H-NMR (400 MHz, CDCl₃) ä 2.35 (s, 6H), 3.67 (s, 3H), 4.70- 4.73 (t, 2H),  6.88 (m, 1H), 6.92- 6.93 (t, 1H), 7.00- 7.01 (J =2 and 8 Hz, s, 2H), 7.09 (t, 1H), 7.29 (d, 3H), 7.62 (t, 2H), 8.11 (s, 1H); ¹³ C NMR (CDCL₃) δ 24.6, 40.7, 51.9, 71.9, 126.6, 128.9, 129.3, 130.1, 135.9, 138.9, 139.9, 140.02, 142.9, 160.9, 171.4; MS m/z 371 (M⁺, 57.98); Anal.Calcd for C₂₅H₂₅NO₂: C, 80.83; H, 6.78; N, 3.77; O, 8.61.  Found: C, 80.56; H, 6.82; N, 3.46; O, 8.56.

Compound 7: To give (0.34 g, 93%); A yellow crystal; Mp: 238; IR (KBr): 3120, 2872, 1720, 1630, 714; ¹ H-NMR (400 MHz, CDCl₃) ä 3.67 (s, 3H), 3.73 (d, 6H), 4.00 (2H), 4.70- 4.73 (t, 2H), 6.59 (m, 1H), 6.63 (m, 1H), 6.68 (J =2 and 8 Hz, t, 1H), 6.72 (m, 2H), 7.01 (s, 2H),   7.10 (d, 1H), 7.29  (t, 3H), 7.62 (J =2 and 8 Hz, t, 2H) , 8.11 (s, 1H); ¹³ C NMR (CDCL₃) δ 40.7, 51.9, 55.9, 71.9, 111.8, 112.3, 114.8, 120.6, 128.9, 129.3, 130.3, 131.2, 135.3, 139.9, 144.2, 158.2, 160.9, 161.2, 171.4; MS m/z 403 (M⁺, 90.16); Anal.Calcd for C₂₅H₂₅NO₄: C, 74.42; H, 6.25; N, 3.47; O, 15.86. Found: C, 74.20; H, 6.30; N, 3.52; O, 15.59.

Compound 8: To give (0.29 g, 81%); A white crystal; Mp: 234; IR (KBr): 3122, 2870, 1721, 1633, 715; ¹ H-NMR (400 MHz, CDCl₃) ä 3.67 (s, 3H), 4.70- 4.73 (J =2 and 8 Hz, t, 2H), 7.08 (m, 2H), 7.12 (m, 4H), 7.21- 7.23 (m, 4H), 7.29 (J =2 and 8 Hz, t, 3H), 7.62 (t, 2H), 8.11  (s, 1H); ¹³ C NMR (CDCL₃)  δ 40.4, 51.9, 71.9, 126.7, 128.9, 129.3, 131.1, 139.9, 160.9, 171.4;   MS m/z 343 (M⁺, 85.12); Anal.Calcd for C₂₃H₂₁NO₂: C, 80.44; H, 6.16; N, 4.08; O, 9.32.  Found: C, 79.54;  H, 6.12; N, 4.12; O, 9.40.

Compound 9: To give (0.30 g, 82%); A white crystal; Mp: 198; IR (KBr): 3125, 2875, 1723, 1637, 710; ¹ H-NMR (400 MHz, CDCl₃) ä 2.35 (s, 3H), 3.65 (s, 3H), 5.20- 5.25 (J =2 and 8 Hz, d, 1H), 6.94 (s, 4H), 7.29 (t, 3H), 7.62- 7.64 (J =2 and 8 Hz, t, 2H), 8.11 (s, 1H);   ¹³ C NMR (CDCL₃) δ 24.3, 51.9, 68.5, 128.9, 129.2, 129.7, 131.1, 135.5, 137.2, 139.9, 16.9, 173; MS m/z 267 (M⁺, 97.13); Anal.Calcd for C₁₇H₁₇NO₂: C, 76.38; H, 6.41; N, 5.24; O, 11.97. Found: C, 76.20; H, 6.20; N, 5.20; O, 11.93.

Compound 10: To give (0.33 g, 90%); A White crystal; Mp: 229; IR (KBr): 3025, 2878, 1729, 1629, 678; ¹ H-NMR (400 MHz, CDCl₃) ä 3.67 (s, 3H), 5.03 (t, 1H), 5.25 (J =2 and 8 Hz, d, 1H), 6.61 (t, 2H),  6.89 (d, 2H), 7.30 (J =2 and 8 Hz, t, 3H), 7.62 (t, 2H), 8.11 (s, 1H); ¹³ C NMR (CDCL₃) δ 51.9, 68.9, 116.3, 128.9, 129.2, 131.1, 139.9, 157.3, 160.9, 173.00; MS m/z 269 (M⁺, 85.45); Anal.Calcd for C₁₆H₁₅NO₃: C, 71.36; H, 5.61; N, 5.20; O, 17.82. Found:  C, 71.20; H, 5.85; N, 5.15; O, 17.80.

Compound 11: To give (0.31 g, 89%); A yellow crystal; Mp: 196; IR (KBr): 3028, 2970, 1730, 1632, 700; ¹ H-NMR (400 MHz, CDCl₃) ä  3.67 (s, 3H), 3.73 (d, 3H), 5.24- 5.25 (J =2 and 8 Hz, d, 1H), 6.65 (2H), 6.95 (s, 4H), 7.28 (t, 3H), 7.63 (t, 2H), 8.10- 8.12 (J =2 and 8 Hz, s, 1H);¹³ C NMR (CDCL₃)  δ 51.9, 55.9, 68.5, 114.7, 128.9, 129.3, 130.8, 131.5, 139.8, 160.9, 173;   MS m/z 283 (M⁺, 90.10); Anal.Calcd for C₁₇H₁₇NO₃: C, 72.07; H, 6.05; N, 4.95; O, 16.94. Found: C, 72.10; H, 6.01; N, 4.90; O, 17.01.

Compound 12: To give (0.34 g, 93%); A white crystal; Mp: 244; IR (KBr): 3032, 2969, 1745, 1660, 723; ¹ H-NMR (400 MHz, CDCl₃) ä 3.69 (s, 3H), 5.23- 5.24 (d, 1H), 6.60 J =2 and 8 Hz, (t, 1H), 6.72 (d, 1H), 6.91 (d, 1H), 7.29 (t, 3H), 7.62 (J =2 and 8 Hz, t, 1H), 8.12 (s, 1H); ¹³ C NMR (CDCL₃) δ 51.8, 68.5, 123.3, 126.9, 128.9, 129.2, 131.5, 139.8, 161.0, 171.5; MS m/z 259 (M⁺, 58.52); Anal.Calcd for C₁₄H₁₃NO₂S: C, 64.84; H, 5.05; N, 5.40; O, 12.58; S, 12.36. Found: C, 64.80; H, 5.12; N, 5.42; O, 12.34; S, 12.20.

Compound 13: To give (0.32 g, 89%); A yellow crystal; Mp: 186; IR (KBr): 3050, 2932, 1739, 1635, 723; ¹ H-NMR (400 MHz, CDCl₃) ä 3.68 (s, 3H), 5.25 (J =2 and 8 Hz, d, 1H), 7.06- 7.07 (m, 3H), 7.14 (m, 2H), 7.30 (t, 3H), 7.62- 7.64 (J =2 and 8 Hz, t, 2H), 8.13 (s, 1H); ¹³ C NMR (CDCL₃) δ 51.7, 68.8, 127.3, 128.5, 129.4, 131.1, 138.4, 139.8, 161.8, 173.5; MS m/z 253  (M⁺, 85.13); Anal.Calcd for C₁₆H₁₅NO₂: C, 75.87; H, 5.97; N, 5.53; O, 12.63. Found: C, 74.95;         H, 5.98; N, 5.10; O, 12.10.

Compound 14: To give (0.27 g, 75%); A brown crystal; Mp: 192; IR (KBr): 3031, 2966, 1747, 1661, 725; ¹ H-NMR (400 MHz, CDCl₃) ä 3.68 (s, 3H), 4.01- 4.05 (J =2 and 8 Hz, t, 2H),5.25 (d, 1H), 6.34 (d, 2H), 6.81- 6.83 (J =2 and 8 Hz, d, 2H), 7.27 (t, 3H), 7.65 (t, 1H), 8.13      (s, 1H); ¹³ C NMR (CDCL₃) δ 51.7, 68.5, 116.8, 128.9, 129.2, 130.6, 138.5, 147.5, 160.9, 171; MS m/z 268 (M⁺, 75.52); Anal.Calcd for C₁₆H₁₆N₂O₂: C, 71.62; H, 6.01; N, 10.44; O, 11.93. Found: C, 71.45; H, 6.10;  N, 10.52; O, 11.85.

Compound 15: To give (0.33 g, 85%); A brown crystal; Mp: 204; 3028, 2970, 1730, 1632, 700;  ¹ H-NMR (400 MHz, CDCl₃) ä 2.35 (s, 3H), 3.67 (s, 3H), 5.25- 5.27 (J =2 and 8 Hz, d, 1H),  7.12 (d, 4H), 7.29 (t, 3H), 7.36- 7.38 (m, 4H), 7.62 (t, 1H), 8.12 (s, 1H); ¹³ C NMR (CDCL₃) δ 24.3, 51.9, 68.5, 127.8, 128.9, 129.2, 131.1, 135.3, 137.4, 139.5, 160.9, 173; MS m/z 343   (M⁺, 58.35); Anal.Calcd for C₂₃H₂₁NO₂: C, 80.44; H, 6.16; N, 4.08; O, 9.32.  Found: C, 80.40; H, 6.12; N, 4.01; O, 9.20.

Compound 16: To give (0.33 g, 92%); A white crystal; Mp: 208; IR (KBr): 3122, 2870, 1721, 1633, 715; ¹ H-NMR (400 MHz, CDCl₃) ä 3.64 (s, 3H), 4.00 (t, 2H), 5.05 (t, 1H), 5.25- 5.27(d, 1H), 6.17 (t, 1H), 6.28- 6.31 (J =2 and 8 Hz, t, 2H), 7.29 (t, 3H), 7.62 (t, 1H), 8.11 (s, 1H);   ¹³ C NMR (CDCL₃) δ 51.7, 59.7, 116.2, 118.1, 123.00, 128.5, 129.8, 131.1, 139.8, 148.9, 160.7, 173.02; MS m/z 284 (M⁺, 90.16); Anal.Calcd for C₁₆H₁₆N₂O₃: C, 67.59; H, 5.67; N, 9.85; O, 16.88. Found: C, 67.54; H, 5.70; N, 9.99; O, 16.75.

Compound 17: To give (0.35 g, 95%); A yellow crystal; Mp: 197; IR (KBr): 3125, 2970, 1725, 1632, 715; ¹ H-NMR (400 MHz, CDCl₃) ä 3.67 (s, 3H), 4.00 (t, 2H), 5.25 (d, 1H), 6.73- 6.79    (s, 1H), 7.07 (t, 1H), 7.27- 7.29 (J =2 and 8 Hz, t, 4H), 7.62 (t, 2H), 8.13 (s, 1H);
¹³ C NMR (CDCL₃) δ 51.9, 58.9, 110.6, 120.1, 122.8, 129.2, 129.7, 131.1, 139.9, 148.5, 150.9, 161.7, 172.9; MS m/z 313 (M⁺, 99.10); Anal.Calcd for C₁₆H₁₅N₃O₄: C, 61.34; H, 4.83; N, 13.41; O, 20.43. Found: C, 61.30; H, 4.90; N, 13.46; O, 20.34.

Compound 18: To give (0.33 g, 90%); A brown crystal; Mp: 188; 3032, 2969, 1745, 1660, 723;  ¹ H-NMR (400 MHz, CDCl₃) ä 3.65 (s, 3H), 5.24- 5.25 (d, 1H), 7.28- 7.29 (J =2 and 8 Hz, t, 3H), 7.32 (t, 2H), 7.62 (t, 2H), 8.07 (d, 2H), 8.12 (s, 1H); ¹³ C NMR (CDCL₃) δ 51.9, 68.8, 121.3, 128.9, 129.8, 130.6, 139.9, 147.5, 160.9, 171; MS m/z 298 (M⁺, 92.18); Anal.Calcd for C₁₆H₁₄N₂O₄: C, 64.42; H, 4.73; N, 9.39; O, 21.50. Found: C, 64.45; H, 4.72; N, 9.40;  O, 21.45.

Compound 19: To give (0.27 g, 75%); A white crystal; Mp: 207; 3125, 2875, 1723, 1637, 710;   ¹ H-NMR (400 MHz, CDCl₃) ä 3.60 (s, 1H), 3.66 (s, 3H), 7.12 (t, 2H), 7.30 (m, 5H),7.36 (m, 2H), 7.50 (d, 1H), 8.00- 8.01 (J =2 and 8 Hz, d, 1H), 8.90 (s, 1H); ¹³ C NMR (CDCL₃)  δ 43.4, 51.9, 119.5, 122.3, 127.9, 130.2, 132.6, 139.5, 143.1, 149.0, 154.8, 163.8, 170.0; MS m/z 336 (M⁺, 95.45); Anal.Calcd for C₁₉H₁₆N₂O₂S: C, 67.84; H, 4.79; N, 8.33; O, 9.51; S, 9.53.   Found: C, 67.80; H, 4.80; N, 8.35; O, 9.45; S, 9.20.

Compound 20: To give (0.38 g, 98%); A yellow crystal; Mp: 296; IR (KBr): 3050, 2932, 1739, 1635, 723; ¹ H-NMR (400 MHz, CDCl₃) ä 2.35 (s, 3H), 3.66 (s, 3H), 5.26 (J =2 and 8 Hz, d, 1H), 7.12 (t, 2H), 7.26 (m, 1H), 7.29 (t, 3H), 7.36 (m, 2H), 7.62  (J =2 and 8 Hz, t, 2H), 8.11 (s, 1H); ¹³ C NMR (CDCL₃) δ 17.9, 51.9, 123.4, 127.3, 128.9, 129.2, 130.5, 131.1, 138.5, 139.9, 160.9, 165.00, 167.1, 173.01; MS m/z 350 (M⁺, 85.16); Anal.Calcd for C₂₀H₁₈N₂O₂S: C, 68.55; H, 5.18; N, 7.99; O, 9.13; S, 9.15. Found: C, 68.75; H, 5.30; N, 8.10; O, 9.20; S, 9.25.

Compound 21: To give (0.33 g, 85%); A yellow crystal; Mp: 202; IR (KBr): 3022, 2923, 1740, 1630, 742; ¹ H-NMR (400 MHz, CDCl₃) ä  3.67 (s, 3H), 3.75(s, 3H), 5.26 (d, 1H), 7.12 (t, 2H), 7.26 (m, 1H), 7.29 (J =2 and 8 Hz, t, 3H), 7.36 (m, 2H), 7.62  (t, 2H), 8.11 (s, 1H); ¹³ C NMR (CDCL₃) δ 51.9, 55.6, 68.5, 123.5, 127.8, 128.6, 129.5, 130.3, 131.1, 132.6, 138.5, 139.8, 157.0, 160.8, 173.1;  MS m/z 366 (M⁺, 93.10); Anal.Calcd for C₂₀H₁₈N₂O₃S: C, 65.55; H, 4.95; N, 7.64; O, 13.10; S, 8.75. Found: C, 64.50; H, 4.98; N, 7.69; O, 12.98; S, 8.70.

Compound 22: To give (0.38 g, 98%); A white crystal; Mp: 204; 3031, 2966, 1747, 1661, 725;   ¹ H-NMR (400 MHz, CDCl₃) ä 3.67 (s, 3H), 5.00 (t, 1H), 5.26 (J =2 and 8 Hz, d, 1H), 7.13 (t, 2H), 7.2 (m, 1H), 7.29 (t, 3H), 7.36 (J =2 and 8 Hz, m, 2H), 7.62  (t, 2H), 8.11 (s, 1H);  ¹³ C NMR (CDCL₃) δ 51.6, 68.5, 123.4, 127.9, 128.8, 129.2, 130.7, 131.4, 132.4, 138.1, 139.9, 157.1, 160.9, 173.4; MS m/z 352 (M⁺, 95.05); Anal.Calcd for C₁₉H₁₆N₂O₃S: C, 64.76; H, 4.58; N, 7.95; O, 13.62; S, 9.10. Found: C, 64.70; H, 4.98; N, 7.69; O, 13.58; S, 9.05.

Result and discussion

Chiral alpha amino acids are widely used in making medicine and poly proteins & poly peptides  and yet much more in  progress  of producing on the way. Late result shows is not easy controllable applying Organic Base in order to preparing Mono Anion to achieve Mono alkylation  instead the result  would be a mixture of mono and di Alkylation products. While to gain the Mono Alkylation products, it needs matching mixing Base & Imine Glycine gradually applying double immiscible solution in which it has Base in water phase and Imine in Organic Phase and the process will gradually transmitting the Base from water phase to Organic Phase in it respond limited forming Anion and formed finally Mono glycine. through these process with Imine synthesis resulted from Benzaldehyde & Methyl ester glycine with present of methyl chloride solution. In this process Color Hydrate glycine salt has been used. The used Base to free the Amine Agent is Three Ethyl Amine.  Remember this transaction with presence of different chemical solution, Salts Bases  and  different temperatures conditions have been researched and study according available documents. Following Amine Synthesis transaction, C- Alkylation from Amino Ester, Glycine Methyl Ester and Benzaldehyde  made at Ednel Conditions. Performed Transaction with ethyl iodide shows probable  combination, but with high degree impurity of both products is possible. It is suggested to continue these process could completed and saved possibly use the phase transfer catalyst  with proper design and Base’s agents which has high different Basic power and also Organic Solutions Phase  followed by heat and saved Alkylation .

Table 1 Click here to View table

 

Figure 1: Click here to View figure

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Figure 2 Click here to View figure

 

Conclusions

The purpose of this project is to prepare the synthetic materials in which they are used in medicine. In This method of preparing Imine could proceed at common room temperature & no need special processing environments conditions. using different types of Alkyl halide to gain different products used in new medicine. And using different type of solutions could effect to improve the production’s process performance quality. Thus using the different types of phase transfer catalyst  for different performances are applied besides of simplicity,  Applying These methods also  speed up the processing mechanism. as the production result proves, high speed composed materials production’s purity formed better and sorting them are much easier.

Acknowledgements

We thanks to Mr. Hanafi for his technical supports in IR Spectroscopy of synthesized products at Islamic Azad University, Shahr rey branch.

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