(S)-1-((R)-2-tert-Butoxycarbonylamino-3,3-dicyclohexyl-propionyl)-pyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: (S)-1-((R)-2-tert-Butoxycarbonylamino-3,3-dicyclohexyl-propionyl)-pyrrolidine-2-carboxylic acid
• CAS No.: 177583-50-5
• Molecular Formula: C₂₅H₄₂N₂O₅
• Molecular Weight: 450.619
• Mol file: 177583-50-5.mol

Synonyms:(S)-1-((R)-2-tert-Butoxycarbonylamino-3,3-dicyclohexyl-propionyl)-pyrrolidine-2-carboxylic acid

Chemical Property of (S)-1-((R)-2-tert-Butoxycarbonylamino-3,3-dicyclohexyl-propionyl)-pyrrolidine-2-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-((R)-2-tert-Butoxycarbonylamino-3,3-dicyclohexyl-propionyl)-pyrrolidine-2-carboxylic acid

There total 8 articles about (S)-1-((R)-2-tert-Butoxycarbonylamino-3,3-dicyclohexyl-propionyl)-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%

(S)-1-((R)-2-tert-Butoxycarbonylamino-3,3-dicyclohexyl-propionyl)-pyrrolidine-2-carboxylic acid methyl ester (183853-44-3) → (S)-1-((R)-2-tert-Butoxycarbonylamino-3,3-dicyclohexyl-propionyl)-pyrrolidine-2-carboxylic acid (177583-50-5)

Guidance literature:

With lithium hydroxide; In methanol; for 3.5h;

DOI:10.1021/jm970493r

Reference yield:

N-(tert-butoxycarbonyl)-3,3-diphenyl-D-alanine (143060-31-5) → (S)-1-((R)-2-tert-Butoxycarbonylamino-3,3-dicyclohexyl-propionyl)-pyrrolidine-2-carboxylic acid (177583-50-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / H₂ / Ir black / aq. acetic acid / 48 h / 3206.3 Torr

2: 97 percent / HOBt, EDC, DIEA / dimethylformamide / 3.5 h

3: 96 percent / aq. LiOH / methanol / 3.5 h

With lithium hydroxide; hydrogen; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; iridium; In methanol; acetic acid; N,N-dimethyl-formamide;

DOI:10.1021/jm970493r

Reference yield:

2-amino-3,3-diphenylpropanoic acid hydrochloride (119273-60-8) → (S)-1-((R)-2-tert-Butoxycarbonylamino-3,3-dicyclohexyl-propionyl)-pyrrolidine-2-carboxylic acid (177583-50-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 66 percent / H₂, aq. AcOH / Ir-black / 48 h / 3206.3 Torr

2: 90 percent / 1N aq. NaOH / dioxane / 2 h / 0 - 20 °C

3: EDC, HOBT, Et₃N / dimethylformamide / 18 h / Ambient temperature

4: 2M aq. LiOH / 1,2-dimethoxy-ethane / 18 h / Ambient temperature

With lithium hydroxide; sodium hydroxide; hydrogen; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; iridium; In 1,4-dioxane; 1,2-dimethoxyethane; N,N-dimethyl-formamide;

DOI:10.1021/jm970140s

upstream raw materials:

(S)-1-((R)-2-tert-Butoxycarbonylamino-3,3-dicyclohexyl-propionyl)-pyrrolidine-2-carboxylic acid methyl ester

N-(tert-butoxycarbonyl)-3,3-diphenyl-D-alanine

(R)-2-tert-butoxycarbonylamino-3,3-dicyclohexyl-propionic acid

di-tert-butyl dicarbonate

Downstream raw materials:

((R)-1-{(S)-2-[(6-Amino-pyridin-3-ylmethyl)-carbamoyl]-pyrrolidine-1-carbonyl}-2,2-dicyclohexyl-ethyl)-carbamic acid tert-butyl ester

((R)-1-{(S)-2-[(6-Amino-2,4-dimethyl-pyridin-3-ylmethyl)-carbamoyl]-pyrrolidine-1-carbonyl}-2,2-dicyclohexyl-ethyl)-carbamic acid tert-butyl ester

((R)-1-{(S)-2-[(2-Amino-thiazol-4-ylmethyl)-carbamoyl]-pyrrolidine-1-carbonyl}-2,2-dicyclohexyl-ethyl)-carbamic acid tert-butyl ester