3-Azabicyclo[3.1.0]hexane-2-carboxaMide, N-[3-aMino-1-(cyclobutylMethyl)-2-hydroxy-3-oxopropyl]-3-[(2S)-2-[[[(1,1 -diMethylethyl)aMino]carbonyl]aMino]-3,3-diMethyl-1-oxobutyl]-6,6-diMe thyl-, (1R,2S,5S)-

Base Information

• Chemical Name: 3-Azabicyclo[3.1.0]hexane-2-carboxaMide, N-[3-aMino-1-(cyclobutylMethyl)-2-hydroxy-3-oxopropyl]-3-[(2S)-2-[[[(1,1 -diMethylethyl)aMino]carbonyl]aMino]-3,3-diMethyl-1-oxobutyl]-6,6-diMe thyl-, (1R,2S,5S)-
• CAS No.: 394735-28-5
• Molecular Formula: C27H47N5O5
• Molecular Weight: 521.701
• Mol file: 394735-28-5.mol

Synonyms:3-Azabicyclo[3.1.0]hexane-2-carboxaMide, N-[3-aMino-1-(cyclobutylMethyl)-2-hydroxy-3-oxopropyl]-3-[(2S)-2-[[[(1,1 -diMethylethyl)aMino]carbonyl]aMino]-3,3-diMethyl-1-oxobutyl]-6,6-diMe thyl-, (1R,2S,5S)-;Hydro-Boceprevir;(1R,2S,5S)-N-[3-Amino-1-(cyclobutylmethyl)-2-hydroxy-3-oxopropyl]-3-[(2S)-2-[[[(1,1-dimethylethyl)amino]carbonyl]amino]-3,3-dimethyl-1-oxobutyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide

Chemical Property of 3-Azabicyclo[3.1.0]hexane-2-carboxaMide, N-[3-aMino-1-(cyclobutylMethyl)-2-hydroxy-3-oxopropyl]-3-[(2S)-2-[[[(1,1 -diMethylethyl)aMino]carbonyl]aMino]-3,3-diMethyl-1-oxobutyl]-6,6-diMe thyl-, (1R,2S,5S)-

Chemical Property:

• PSA: 153.86000
• LogP: 3.31390

Purity/Quality:

95%, 99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-Azabicyclo[3.1.0]hexane-2-carboxaMide, N-[3-aMino-1-(cyclobutylMethyl)-2-hydroxy-3-oxopropyl]-3-[(2S)-2-[[[(1,1 -diMethylethyl)aMino]carbonyl]aMino]-3,3-diMethyl-1-oxobutyl]-6,6-diMe thyl-, (1R,2S,5S)-

There total 76 articles about 3-Azabicyclo[3.1.0]hexane-2-carboxaMide, N-[3-aMino-1-(cyclobutylMethyl)-2-hydroxy-3-oxopropyl]-3-[(2S)-2-[[[(1,1 -diMethylethyl)aMino]carbonyl]aMino]-3,3-diMethyl-1-oxobutyl]-6,6-diMe thyl-, (1R,2S,5S)- 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: 99.0%

3-amino-4-cyclobutyl-2-hydroxybutanamide hydrochloride (1036931-36-8,1996616-36-4,394735-23-0,1036931-35-7) + (1R,2S,5S)-3-((S)-2-(3-tert-butylureido)-3,3-dimethylbutanoyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid (816444-90-3) → (1R,2S,5S)-N-(4-amino-1-cyclobutyl-3-hydroxy-4-oxobutan-2-yl)-3-((S)-2-(3-(tert-butyl)ureido)-3,3-dimethylbutanoyl)-6,6-dimethyl-3-azabicylo[3.1.0]-hexane-2-carboxamide (394735-28-5)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In 1-methyl-pyrrolidin-2-one; water; ethyl acetate; at 20 - 24 ℃; for 16h;

Reference yield: 92.3%

C34H53N5O5 → (1R,2S,5S)-N-(4-amino-1-cyclobutyl-3-hydroxy-4-oxobutan-2-yl)-3-((S)-2-(3-(tert-butyl)ureido)-3,3-dimethylbutanoyl)-6,6-dimethyl-3-azabicylo[3.1.0]-hexane-2-carboxamide (394735-28-5)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 40 ℃; under 5250.53 Torr;

Reference yield: 90.4%

3-amino-4-cyclobutyl-2-hydroxybutanamide hydrochloride (1036931-36-8,1996616-36-4,394735-23-0,1036931-35-7) + C8H17N*C19H33N3O4 (1034917-71-9) → (1R,2S,5S)-N-(4-amino-1-cyclobutyl-3-hydroxy-4-oxobutan-2-yl)-3-((S)-2-(3-(tert-butyl)ureido)-3,3-dimethylbutanoyl)-6,6-dimethyl-3-azabicylo[3.1.0]-hexane-2-carboxamide (394735-28-5)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In water; ethyl acetate; N,N-dimethyl-formamide; at 0 - 25 ℃; for 5.5h; Product distribution / selectivity; Industry scale;

upstream raw materials:

3-amino-4-cyclobutyl-2-hydroxybutanamide hydrochloride

(1R,2S,5S)-3-((S)-2-(3-tert-butylureido)-3,3-dimethylbutanoyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid

(2-cyclobutyl-1-formylethyl)carbamic acid tert-butyl ester

(2-cyano-1-cyclobutylmethyl-2-hydroxyethyl)carbamic acid tert-butyl ester

Downstream raw materials:

(1R,2S,5S)-3-((S)-2-(3-tert-butylureido)-3,3-dimethylbutanoyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid

boceprevir

Refernces

• 1、 -. "Anti-hepatitis c drug Boceprevir intermediates III and its preparation method and application". . . Retrieved 2017/02/02.
• 2、 -. "Anti-hepatitis c drug Boceprevir intermediate VIII and its preparation method and application". Paragraph 0160-0162. . Retrieved 2016/11/28.