1-{(2R)-2-[(tert-butoxycarbonyl)amino]-2-cyclohexylethanoyl}-L-proline

Base Information

• Chemical Name: 1-{(2R)-2-[(tert-butoxycarbonyl)amino]-2-cyclohexylethanoyl}-L-proline
• CAS No.: 146621-94-5
• Molecular Formula: C18H30N2O5
• Molecular Weight: 354.447
• DSSTox Substance ID: DTXSID601166241
• Mol file: 146621-94-5.mol

Synonyms:146621-94-5;1-{(2R)-2-[(tert-butoxycarbonyl)amino]-2-cyclohexylethanoyl}-L-proline;SCHEMBL6077122;GXJFWLZSFRQBML-UONOGXRCSA-N;DTXSID601166241;(2R)-2-Cyclohexyl-N-[(1,1-dimethylethoxy)carbonyl]glycyl-L-proline

Chemical Property of 1-{(2R)-2-[(tert-butoxycarbonyl)amino]-2-cyclohexylethanoyl}-L-proline

Chemical Property:

• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 354.21547206
• Heavy Atom Count: 25
• Complexity: 508

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(C1CCCCC1)C(=O)N2CCCC2C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](C1CCCCC1)C(=O)N2CCC[C@H]2C(=O)O

Technology Process of 1-{(2R)-2-[(tert-butoxycarbonyl)amino]-2-cyclohexylethanoyl}-L-proline

There total 3 articles about 1-{(2R)-2-[(tert-butoxycarbonyl)amino]-2-cyclohexylethanoyl}-L-proline 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: 92.0%

(S)-benzyl 1-((R)-2-(tert-butoxycarbonylamino)-2-cyclohexylacetyl)pyrrolidine-2-carboxylate (1215172-54-5) → (S)-1-((R)-2-(tert-butoxycarbonylamino)-2-cyclohexylacetyl)pyrrolidine-2-carboxylic acid (146621-94-5)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; under 2585.81 - 2844.39 Torr;

DOI:10.1021/jm9016416

Reference yield:

N-Boc-Chg-Pro-OMe (190509-47-8) → (S)-1-((R)-2-(tert-butoxycarbonylamino)-2-cyclohexylacetyl)pyrrolidine-2-carboxylic acid (146621-94-5)

Guidance literature:

With lithium hydroxide; In 1,2-dimethoxyethane; for 18h; Yield given; Ambient temperature;

DOI:10.1021/jm9801713

Reference yield:

(2R)-[(tert-butoxycarbonyl)-amino](cyclohexyl)ethanoic acid (70491-05-3) → (S)-1-((R)-2-(tert-butoxycarbonylamino)-2-cyclohexylacetyl)pyrrolidine-2-carboxylic acid (146621-94-5)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With lithium hydroxide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In 1,2-dimethoxyethane; N,N-dimethyl-formamide;

DOI:10.1021/jm9801713

upstream raw materials:

N-Boc-Chg-Pro-OMe

(2R)-[(tert-butoxycarbonyl)-amino](cyclohexyl)ethanoic acid

(S)-benzyl 1-((R)-2-(tert-butoxycarbonylamino)-2-cyclohexylacetyl)pyrrolidine-2-carboxylate

Downstream raw materials:

{(R)-1-Cyclohexyl-2-[(S)-2-(2,5-dichloro-benzylcarbamoyl)-pyrrolidin-1-yl]-2-oxo-ethyl}-carbamic acid tert-butyl ester

{(R)-2-[(S)-2-(5-Chloro-2-hydroxy-benzylcarbamoyl)-pyrrolidin-1-yl]-1-cyclohexyl-2-oxo-ethyl}-carbamic acid tert-butyl ester

C₃₄H₄₅N₅O₆

Refernces

• 1、 Muley, Laveena,Baum, Bernhard,Smolinski, Michael,Freindorf, Marek,Heine, Andreas,Klebe, Gerhard,Hangauer, David G.. "Enhancement of hydrophobic interactions and hydrogen bond strength by cooperativity: Synthesis, modeling, and molecular dynamics simulations of a congeneric series of thrombin inhibitors". supporting information; experimental part. p. 2126 - 2135. Retrieved 2010/08/19.