[S-(R*,R*)]-2-[[[1-[[(2-Amino-2-oxoethyl)thio]methyl]-3-methylbutyl][(1,1-Dimethylethoxy)carbonyl]amino]methyl]-1-[pyrrolidine]carboxylic acid, phenylmethyl ester

Base Information

• Chemical Name: [S-(R*,R*)]-2-[[[1-[[(2-Amino-2-oxoethyl)thio]methyl]-3-methylbutyl][(1,1-Dimethylethoxy)carbonyl]amino]methyl]-1-[pyrrolidine]carboxylic acid, phenylmethyl ester
• CAS No.: 101250-68-4
• Molecular Formula: C₂₆H₄₁N₃O₅S
• Molecular Weight: 507.695
• Mol file: 101250-68-4.mol

Synonyms:[S-(R*,R*)]-2-[[[1-[[(2-Amino-2-oxoethyl)thio]methyl]-3-methylbutyl][(1,1-Dimethylethoxy)carbonyl]amino]methyl]-1-[pyrrolidine]carboxylic acid, phenylmethyl ester

Chemical Property of [S-(R*,R*)]-2-[[[1-[[(2-Amino-2-oxoethyl)thio]methyl]-3-methylbutyl][(1,1-Dimethylethoxy)carbonyl]amino]methyl]-1-[pyrrolidine]carboxylic acid, phenylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [S-(R*,R*)]-2-[[[1-[[(2-Amino-2-oxoethyl)thio]methyl]-3-methylbutyl][(1,1-Dimethylethoxy)carbonyl]amino]methyl]-1-[pyrrolidine]carboxylic acid, phenylmethyl ester

There total 6 articles about [S-(R*,R*)]-2-[[[1-[[(2-Amino-2-oxoethyl)thio]methyl]-3-methylbutyl][(1,1-Dimethylethoxy)carbonyl]amino]methyl]-1-[pyrrolidine]carboxylic acid, phenylmethyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 69.0%

[S-(R*,R*)]-2-[[[1-[[(Carboxymethyl)thio]methyl]-3-methylbutyl][(1,1-dimethylethoxy)carbonyl]amino]methyl]-1-pyrrolidinecarboxylic acid, phenylmethyl ester (104379-84-2) + isobutyl chloroformate (543-27-1) → [S-(R*,R*)]-2-[[[1-[[(2-Amino-2-oxoethyl)thio]methyl]-3-methylbutyl][(1,1-Dimethylethoxy)carbonyl]amino]methyl]-1-[pyrrolidine]carboxylic acid, phenylmethyl ester (101250-68-4)

Guidance literature:

With 4-methyl-morpholine; In tetrahydrofuran;

Reference yield:

(S)-2-(2-Methylpropyl)-aziridine (23852-57-5) → [S-(R*,R*)]-2-[[[1-[[(2-Amino-2-oxoethyl)thio]methyl]-3-methylbutyl][(1,1-Dimethylethoxy)carbonyl]amino]methyl]-1-[pyrrolidine]carboxylic acid, phenylmethyl ester (101250-68-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 55 percent / H₂S / ethanol / -78 - 25 °C

2: 43 percent / NH₃ liquid

3: 1.) 5A molecular sieves, 2.) bromocresol, NaCNBH₃, HCl gas / 1.) THF, overnight, 2.) EtOH, 25 deg C, 2 d

4: 44 percent / trifluoroacetic acid (TFA)

5: 2.) isobutyl chloroformate, 3.) NH₃

With hydrogenchloride; 5A molecular sieve; 2-bromo-6-methylphenol; hydrogen sulfide; ammonia; sodium cyanoborohydride; trifluoroacetic acid; isobutyl chloroformate; In ethanol;

DOI:10.1021/jm00156a012

Reference yield:

(S)-2-amino-4-methyl-1-pentanethiol (88264-65-7) → [S-(R*,R*)]-2-[[[1-[[(2-Amino-2-oxoethyl)thio]methyl]-3-methylbutyl][(1,1-Dimethylethoxy)carbonyl]amino]methyl]-1-[pyrrolidine]carboxylic acid, phenylmethyl ester (101250-68-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 43 percent / NH₃ liquid

2: 1.) 5A molecular sieves, 2.) bromocresol, NaCNBH₃, HCl gas / 1.) THF, overnight, 2.) EtOH, 25 deg C, 2 d

3: 44 percent / trifluoroacetic acid (TFA)

4: 2.) isobutyl chloroformate, 3.) NH₃

With hydrogenchloride; 5A molecular sieve; 2-bromo-6-methylphenol; ammonia; sodium cyanoborohydride; trifluoroacetic acid; isobutyl chloroformate;

DOI:10.1021/jm00156a012

upstream raw materials:

di-tert-butyl dicarbonate

*,R^*)>-phenylmethyl 2-<<<1-<<(carboxymethyl)thio>methyl>-3-methylbutyl>amino>methyl>-1-pyrrolidinecarboxylate

(S)-2-(2-Methylpropyl)-aziridine

(S)-2-amino-4-methyl-1-pentanethiol

Downstream raw materials:

*,R^*)>-phenylmethyl 2-<<<1-<<(2-amino-2-oxoethyl)thio>methyl>-3-methylbutyl>amino>methyl>-1-pyrrolidinecarboxylate hydrochloride