(2S,4S,5S)-1-(4-(tert-butyl)-3-methoxybenzoyl)-2-isobutyl-4-(methoxymethyl)-5-(thiazol-2-yl)pyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: (2S,4S,5S)-1-(4-(tert-butyl)-3-methoxybenzoyl)-2-isobutyl-4-(methoxymethyl)-5-(thiazol-2-yl)pyrrolidine-2-carboxylic acid
• CAS No.: 687637-40-7
• Molecular Formula: C₂₆H₃₆N₂O₅S
• Molecular Weight: 488.648
• Mol file: 687637-40-7.mol

Synonyms:

Chemical Property of (2S,4S,5S)-1-(4-(tert-butyl)-3-methoxybenzoyl)-2-isobutyl-4-(methoxymethyl)-5-(thiazol-2-yl)pyrrolidine-2-carboxylic acid

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S,5S)-1-(4-(tert-butyl)-3-methoxybenzoyl)-2-isobutyl-4-(methoxymethyl)-5-(thiazol-2-yl)pyrrolidine-2-carboxylic acid

There total 36 articles about (2S,4S,5S)-1-(4-(tert-butyl)-3-methoxybenzoyl)-2-isobutyl-4-(methoxymethyl)-5-(thiazol-2-yl)pyrrolidine-2-carboxylic acid 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: 96.0%

tert-butyl (2S,4S,5S)-1-(4-(tert-butyl)-3-methoxybenzoyl)-2-isobutyl-4-(methoxymethyl)-5-(thiazol-2-yl)pyrrolidine-2-carboxylate → (2S,4S,5S)-1-(4-(tert-butyl)-3-methoxybenzoyl)-2-isobutyl-4-(methoxymethyl)-5-(thiazol-2-yl)pyrrolidine-2-carboxylic acid (687637-40-7)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 14h;

DOI:10.1016/j.ejmech.2019.03.019

Reference yield:

rel-(2S,4S,5R)-2-isobutyl-1-(3-methoxy-4-tert-butylbenzoyl)-4-methoxymethyl-5-(1,3-thiazol-2-yl)pyrrolidine-2-carboxylic acid tert-butyl ester → rel-(2S,4S,5R)-2-isobutyl-1-(3-methoxy-4-tert-butylbenzoyl)-4-methoxymethyl-5-(1,3-thiazol-2-yl)pyrrolidine-2-carboxylic acid (687637-40-7)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃;

Reference yield:

2-[N-(1,3-thiazol-2-ylmethylene)amino]-4-methylpentanoic acid tert-butyl ester (521955-41-9) → (4S,5R)-1-{[4-(1,1-dimethylethyl)-3-(methoxy)phenyl]carbonyl}-4-(hydroxymethyl)-2-(2-methylpropyl)-5-(1,3-thiazol-2-yl)-L-proline (687637-40-7)

Guidance literature:

Multi-step reaction with 6 steps

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

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

3.1: 98 percent / triethylamine / CH₂Cl₂ / 19 h / 0 - 20 °C

4.1: 85 percent / LiAlH₄ / tetrahydrofuran / 5 h / -78 - -20 °C

5.1: sodium hydride / dimethylformamide / 0.33 h / -15 °C

5.2: 57 percent / dimethylformamide / 24 h / -15 - 10 °C

6.1: 86 percent / trifluoroacetic acid / CH₂Cl₂ / 18 h / 20 °C

With lithium aluminium tetrahydride; (R)-1,1'-binaphthyl-2,2'-phosphoric acid; sodium hydride; triethylamine; trifluoroacetic acid; lithium bromide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1021/jm061207r

upstream raw materials:

(2S,4S,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

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

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