tert-butyl ((R)-1-((2S)-2-((4-cyanobenzyl)carbamoyl)pyrrolidin-1-yl)-1-cyclohexyl-2-oxoethyl)carbamate

Base Information

• Chemical Name: tert-butyl ((R)-1-((2S)-2-((4-cyanobenzyl)carbamoyl)pyrrolidin-1-yl)-1-cyclohexyl-2-oxoethyl)carbamate
• CAS No.: 171846-10-9
• Molecular Formula: C₂₆H₃₆N₄O₄
• Molecular Weight: 468.596
• Mol file: 171846-10-9.mol

Synonyms:tert-butyl ((R)-1-((2S)-2-((4-cyanobenzyl)carbamoyl)pyrrolidin-1-yl)-1-cyclohexyl-2-oxoethyl)carbamate

Chemical Property of tert-butyl ((R)-1-((2S)-2-((4-cyanobenzyl)carbamoyl)pyrrolidin-1-yl)-1-cyclohexyl-2-oxoethyl)carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl ((R)-1-((2S)-2-((4-cyanobenzyl)carbamoyl)pyrrolidin-1-yl)-1-cyclohexyl-2-oxoethyl)carbamate

There total 8 articles about tert-butyl ((R)-1-((2S)-2-((4-cyanobenzyl)carbamoyl)pyrrolidin-1-yl)-1-cyclohexyl-2-oxoethyl)carbamate 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: 100.0%

4-aminobenzyl cyanide (10406-25-4) + (S)-1-((R)-2-(tert-butoxycarbonylamino)-2-cyclohexylacetyl)pyrrolidine-2-carboxylic acid (146621-94-5) → tert-butyl ((R)-1-((2S)-2-((4-cyanobenzyl)carbamoyl)pyrrolidin-1-yl)-1-cyclohexyl-2-oxoethyl)carbamate (171846-10-9)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide;

DOI:10.1016/S0960-894X(02)00093-8

Reference yield: 56.0%

(S)-N-(4-cyanobenzyl)pyrrolidine-2-carboxamide hydrochloride + (2R)-[(tert-butoxycarbonyl)-amino](cyclohexyl)ethanoic acid (70491-05-3) → tert-butyl ((R)-1-((2S)-2-((4-cyanobenzyl)carbamoyl)pyrrolidin-1-yl)-1-cyclohexyl-2-oxoethyl)carbamate (171846-10-9)

Guidance literature:

With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 16h;

DOI:10.1016/j.ejmech.2015.03.059

Reference yield:

para-methylbenzonitrile (104-85-8) → tert-butyl ((R)-1-((2S)-2-((4-cyanobenzyl)carbamoyl)pyrrolidin-1-yl)-1-cyclohexyl-2-oxoethyl)carbamate (171846-10-9)

Guidance literature:

Multi-step reaction with 4 steps

1: NBS; benzoylperoxide / CCl₄ / Heating

2: NaH / tetrahydrofuran

3: TFA / CH₂Cl₂

4: 100 percent / NMM; EDC; HOBT

With 4-methyl-morpholine; N-Bromosuccinimide; sodium hydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; dibenzoyl peroxide; In tetrahydrofuran; tetrachloromethane; dichloromethane; 2: Gabriel-type amination;

DOI:10.1016/S0960-894X(02)00093-8

upstream raw materials:

4-aminobenzyl cyanide

(S)-1-((R)-2-(tert-butoxycarbonylamino)-2-cyclohexylacetyl)pyrrolidine-2-carboxylic acid

para-methylbenzonitrile

4-cyanobenzyl bromide

Downstream raw materials:

C₂₆H₃₉N₅O₄

(S)-1-((R)-2-Cyclohexyl-2-methanesulfonylamino-acetyl)-pyrrolidine-2-carboxylic acid 4-cyano-benzylamide