D-Proline, 1-[4-(1,1-dimethylethyl)-3-methoxybenzoyl]-4-(hydroxymethyl)-2-(2-meth ylpropyl)-5-(2-thiazolyl)-, (4R,5R)-

Base Information

• Chemical Name: D-Proline, 1-[4-(1,1-dimethylethyl)-3-methoxybenzoyl]-4-(hydroxymethyl)-2-(2-meth ylpropyl)-5-(2-thiazolyl)-, (4R,5R)-
• CAS No.: 927436-24-6
• Molecular Formula: C25H34N2O5S
• Molecular Weight: 530.729
• Mol file: 927436-24-6.mol

Synonyms:

Chemical Property of D-Proline, 1-[4-(1,1-dimethylethyl)-3-methoxybenzoyl]-4-(hydroxymethyl)-2-(2-meth ylpropyl)-5-(2-thiazolyl)-, (4R,5R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of D-Proline, 1-[4-(1,1-dimethylethyl)-3-methoxybenzoyl]-4-(hydroxymethyl)-2-(2-meth ylpropyl)-5-(2-thiazolyl)-, (4R,5R)-

There total 5 articles about D-Proline, 1-[4-(1,1-dimethylethyl)-3-methoxybenzoyl]-4-(hydroxymethyl)-2-(2-meth ylpropyl)-5-(2-thiazolyl)-, (4R,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: 70.0%

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 (687636-13-1) → 1,1-dimethylethyl (4S,5R)-1-{[4-(1,1-dimethylethyl)-3-(methyloxy)phenyl]carbonyl}-4-(hydroxymethyl)-2-(2-methylpropyl)-5-(1,3-thiazol-2-yl)-L-prolinate (687636-14-2) + (2S,4R,5R)-2-isobutyl-1-(3-methoxy-4-tert-butylbenzoyl)-4-hydroxymethyl-5-(1,3-thiazol-2-yl)-pyrrolidine-2-carboxylic acid 2-tert-butyl ester (927436-24-6)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; at 20 ℃; for 16h;

DOI:10.1021/jm061207r

Reference yield:

2-[N-(1,3-thiazol-2-ylmethylene)amino]-4-methylpentanoic acid tert-butyl ester (521955-41-9) → (2S,4R,5R)-2-isobutyl-1-(3-methoxy-4-tert-butylbenzoyl)-4-hydroxymethyl-5-(1,3-thiazol-2-yl)-pyrrolidine-2-carboxylic acid 2-tert-butyl ester (927436-24-6)

Guidance literature:

Multi-step reaction with 4 steps

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

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

3: 98 percent / triethylamine / CH₂Cl₂ / 19 h / 0 - 20 °C

4: 70 percent / lithium borohydride / tetrahydrofuran / 16 h / 20 °C

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

DOI:10.1021/jm061207r

Reference yield:

2-(1,1-dimethylethyl) 4-methyl (2RS,4RS,5SR)-2-(2-methylpropyl)-5-(1,3-thiazol-2-yl)-2,4-pyrrolidinedicarboxylate → (2S,4R,5R)-2-isobutyl-1-(3-methoxy-4-tert-butylbenzoyl)-4-hydroxymethyl-5-(1,3-thiazol-2-yl)-pyrrolidine-2-carboxylic acid 2-tert-butyl ester (927436-24-6)

Guidance literature:

Multi-step reaction with 3 steps

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

2: 98 percent / triethylamine / CH₂Cl₂ / 19 h / 0 - 20 °C

3: 70 percent / lithium borohydride / tetrahydrofuran / 16 h / 20 °C

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

DOI:10.1021/jm061207r

upstream raw materials:

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

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

2-(1,1-dimethylethyl) 4-methyl (2S,4S,5R)-2-(2-methylpropyl)-5-(1,3-thiazol-2-yl)-2,4-pyrrolidinedicarboxylate

leucine tert-butyl ester hydrochloride

Downstream raw materials:

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

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