394735-27-4

Basic information

• Product Name: (1S,2S,5R)-Methyl 3-((S)-2-(tert-butoxycarbonylaMino)-3,3-diMethylbutanoyl)-6,6-diMethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate
• Synonyms: (1S,2S,5R)-Methyl 3-((S)-2-(tert-butoxycarbonylaMino)-3,3-diMethylbutanoyl)-6,6-diMethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate;(1S,2S,5R)-Methyl 3-((S)-2-(3-(tert-butyl)ureido)-3,3-diMethylbutanoyl)-6,6-diMethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate;3-Azabicyclo[3.1.0]hexane-2-carboxylic acid, 3-[(2S)-2-[[[(1,1-diMethylethyl)aMino]carbonyl]aMino]-3,3-diMethyl-1-ox obutyl]-6,6-diMethyl-, Methyl ester, (1R,2S,5S)-;(1R,2S,5S)-3-[(2S)-2-[[[(1,1-Dimethylethyl)amino]carbonyl]amino]-3,3-dimethyl-1-oxobutyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid methyl ester;methyl (1S,2S,5R)-3-[(2S)-2-(tert-butoxycarbonylamino)-3,3-dimeth yl-butanoyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate
• CAS NO: 394735-27-4
• Molecular Formula: C₂₀H₃₅N₃O₄
• Molecular Weight: 382.49436
• Mol File: 394735-27-4.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 529.4±35.0 °C(Predicted)
• Appearance: /
• Density: 1.091±0.06 g/cm3(Predicted)
• PKA: 13.46±0.46(Predicted)
• CAS DataBase Reference: (1S,2S,5R)-Methyl 3-((S)-2-(tert-butoxycarbonylaMino)-3,3-diMethylbutanoyl)-6,6-diMethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S,5R)-Methyl 3-((S)-2-(tert-butoxycarbonylaMino)-3,3-diMethylbutanoyl)-6,6-diMethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate(394735-27-4)
• EPA Substance Registry System: (1S,2S,5R)-Methyl 3-((S)-2-(tert-butoxycarbonylaMino)-3,3-diMethylbutanoyl)-6,6-diMethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate(394735-27-4)

Safety Data

• Hazardous Substances Data: 394735-27-4(Hazardous Substances Data)

Usage

General Description

The chemical "(1S,2S,5R)-Methyl 3-((S)-2-(tert-butoxycarbonylaMino)-3,3-diMethylbutanoyl)-6,6-diMethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate" is a complex organic compound. It is derived from 3-azabicyclo[3.1.0]hexane and contains a carboxylate group. The compound also contains a tert-butoxycarbonyl group, which is a protecting group for amines, and a 3,3-dimethylbutanoyl group. The structure of the compound includes three chiral centers, resulting in a stereochemically complex molecule. The compound may have potential applications in pharmaceutical or organic chemistry research due to its unique structural features.

Upstream product

• 20859-02-3 L-tert-Leucine 
• 62965-35-9 N-tert-butyloxycarbonyl-L-tert-leucine 
• 2425-74-3 t-butylformamide 
• 101968-85-8 (S)-2-(3-(tert-butyl)ureido)-3,3-dimethylbutanoic acid 
• 219753-99-8 (1S,2S,4S,7R)-6-aza-3,3-dimethyl-8-oxa-7-phenyltricyclo<4.3.0.0>nonan-5-one 
• 219754-02-6 (1R,2S,5S)-3-(tert-butoxycarbonyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid 
• 219754-00-4 tert-butyl (1R,2S,5S)-2-(hydroxymethyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-3-carboxylate 
• 1026427-11-1 ((1R,2S,5S)-3-Benzyl-6,6-dimethyl-3-aza-bicyclo[3.1.0]hex-2-yl)-methanol 
• 103201-79-2 (3R,7aS)-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one 
• 134107-65-6 (3R,7aS)-3-phenyl-3,7a-dihydro-1H-pyrrolo[1,2-c]oxazol-5-one 
• 394735-26-3 (1R,2S,5S)-3-((S)-2-tert-Butoxycarbonylamino-3,3-dimethyl-butyryl)-6,6-dimethyl-3-aza-bicyclo[3.1.0]hexane-2-carboxylic acid methyl ester 
• 569679-06-7 3-(tert-butyl) 2-methyl (1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2,3-dicarboxylate 
• 1609-86-5 Tert-butyl isocyanate 

Downstream Products

• 394735-28-5 (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 
• 394730-60-0 boceprevir 
• 816444-90-3 (1R,2S,5S)-3-((S)-2-(3-tert-butylureido)-3,3-dimethylbutanoyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid 

Relevant articles and documents

Synthesis and Process Optimization of Boceprevir: A Protease Inhibitor Drug

Efforts toward the synthesis and process optimization of boceprevir 1 are described. Boceprevir synthesis was optimized by telescoping the first three steps and last two steps of the five-step process. Optimization of oxidation, which is one of the critical steps in the total synthesis, is discussed. A control strategy for the three impurities is described. A novel process for the synthesis of fragment A (2) has been developed, which is the key starting material for the synthesis of boceprevir.

Design and synthesis of deuterated boceprevir analogs with enhanced pharmacokinetic properties

As part of an ongoing effort to apply the Deuterated Chemical Entity Platform (DCE Platforma) to clinically validated drugs, the synthesis of deuterated analogs of the hepatitis C virus protease inhibitor boceprevir was carried out. The devised synthetic routes allowed for site-selective deuterium incorporation with high levels of isotopic purity. Application of the DCE Platforma to boceprevir enabled the identification of several deuterated analogs that display marked levels of in vitro metabolic stabilization. Most notably, analog 1g exhibits a near doubling of in vitro half-life in human liver microsomal assays. The details of the convergent synthetic route to the boceprevir isotopologs and the results of the metabolic stability assays are described herein.

PROCESS FOR PREPARING (1R,2S,5S)-N-[(1S)-3-AMINO-1-(CYCLOBUTYLMETHYL)-2,3-DIOXOPROPYL]-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

The present invention relates also to a process for the preparation of intermediate compounds useful in preparing the compounds of Formula (I) using the process of Scheme (II).