2,4-Pyrrolidinedicarboxylic acid, 2-(2-methylpropyl)-5-(2-thiazolyl)-, 2-(1,1-dimethylethyl) 4-methyl ester, (2S,4S,5R)-

Base Information

• Chemical Name: 2,4-Pyrrolidinedicarboxylic acid, 2-(2-methylpropyl)-5-(2-thiazolyl)-, 2-(1,1-dimethylethyl) 4-methyl ester, (2S,4S,5R)-
• CAS No.: 687636-12-0
• Molecular Formula: C18H28N2O4S
• Molecular Weight: 368.497
• Mol file: 687636-12-0.mol

Synonyms:

Chemical Property of 2,4-Pyrrolidinedicarboxylic acid, 2-(2-methylpropyl)-5-(2-thiazolyl)-, 2-(1,1-dimethylethyl) 4-methyl ester, (2S,4S,5R)-

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,4-Pyrrolidinedicarboxylic acid, 2-(2-methylpropyl)-5-(2-thiazolyl)-, 2-(1,1-dimethylethyl) 4-methyl ester, (2S,4S,5R)-

There total 6 articles about 2,4-Pyrrolidinedicarboxylic acid, 2-(2-methylpropyl)-5-(2-thiazolyl)-, 2-(1,1-dimethylethyl) 4-methyl ester, (2S,4S,5R)- 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:

2-(1,1-dimethylethyl) 4-methyl (2RS,4RS,5SR)-2-(2-methylpropyl)-5-(1,3-thiazol-2-yl)-2,4-pyrrolidinedicarboxylate → 2-(1,1-dimethylethyl) 4-methyl (2S,4S,5R)-2-(2-methylpropyl)-5-(1,3-thiazol-2-yl)-2,4-pyrrolidinedicarboxylate (687636-12-0)

Guidance literature:

With (R)-1,1'-binaphthyl-2,2'-phosphoric acid; In isopropyl alcohol; at 75 ℃;

DOI:10.1021/jm061207r

Reference yield:

tert-butyl (S,E)-4-methyl-2-((thiazol-2-ylmethylene)amino)pentanoate + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → 2-(1,1-dimethylethyl) 4-methyl (2S,4S,5R)-2-(2-methylpropyl)-5-(1,3-thiazol-2-yl)-2,4-pyrrolidinedicarboxylate (687636-12-0) + 2-(1,1-dimethylethyl) 4-methyl (2R,4R,5S)-2-(2-methylpropyl)-5-(1,3-thiazol-2-yl)-2,4-pyrrolidinedicarboxylate

Guidance literature:

tert-butyl (S,E)-4-methyl-2-((thiazol-2-ylmethylene)amino)pentanoate; With 4 A molecular sieve; silver(I) acetate; dihydroquinine; In toluene; at 0 ℃; for 0.25h;

acrylic acid methyl ester; In toluene; at 0 - 20 ℃; Further stages. Title compound not separated from byproducts.;

DOI:10.1021/jo800062c

Reference yield:

2-[N-(1,3-thiazol-2-ylmethylene)amino]-4-methylpentanoic acid tert-butyl ester (521955-41-9) → 2-(1,1-dimethylethyl) 4-methyl (2S,4S,5R)-2-(2-methylpropyl)-5-(1,3-thiazol-2-yl)-2,4-pyrrolidinedicarboxylate (687636-12-0)

Guidance literature:

Multi-step reaction with 2 steps

1: lithium bromide; triethylamine / tetrahydrofuran / 20 °C

2: (R)-(-)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate / propan-2-ol / 75 °C

With (R)-1,1'-binaphthyl-2,2'-phosphoric acid; triethylamine; lithium bromide; In tetrahydrofuran; isopropyl alcohol;

DOI:10.1021/jm061207r

upstream raw materials:

2-[N-(1,3-thiazol-2-ylmethylene)amino]-4-methylpentanoic acid tert-butyl ester

leucine tert-butyl ester hydrochloride

acrylic acid methyl ester

Downstream raw materials:

(2S,4S,5R)-2-isobutyl-1-(3-methyl-4-tert-butylbenzoyl)-5-(1,3-thiazol-2-yl)-pyrrolidine-2,4-dicarboxylic acid 2-tert-butyl ester 4-methyl ester

2-(1,1-dimethylethyl) 4-methyl (2S,4S,5R)-1-{[4-(1,1-dimethylethyl)-3-(methoxy)phenyl]carbonyl}-2-(2-methylpropyl)-5-(1,3-thiazol-2-yl)-2,4-pyrrolidinedicarboxylate

(4S,5R)-1-{[4-(1,1-dimethylethyl)-3-(methoxy)phenyl]carbonyl}-4-(hydroxymethyl)-2-(2-methylpropyl)-5-(1,3-thiazol-2-yl)-L-proline

(2S,4R,5R)-2-isobutyl-1-(3-methoxy-4-tert-butylbenzoyl)-4-methoxymethyl-5-(1,3-thiazol-2-yl)pyrrolidine-2-carboxylic acid