197142-36-2

Basic information

• Product Name: (1S,3S,5S)-2-(TERT-BUTOXYCARBONYL)-2-AZABICYCLO[3.1.0]HEXANE-3-CARBOXYLIC ACID
• Synonyms: (1S,3S,5S)-2-(TERT-BUTOXYCARBONYL)-2-AZABICYCLO[3.1.0]HEXANE-3-CARBOXYLIC ACID;(1s,3s,5s)-2-boc-2-azabicyclo[3.1.0]hexane-3-carboxylic acid;N-Boc-L-cis-4,5-methanoproline;-2-azabicyclo[3.1.0]hexane-3-carboxylic acid;(1S,3S,5S)-2-Boc-2-aza-bicyclo[3.1.0]hexane-3-dicarboxylic acid
• CAS NO: 197142-36-2
• Molecular Formula: C₁₁H₁₇NO₄
• Molecular Weight: 227.25698
• Mol File: 197142-36-2.mol

Chemical Properties

• Boiling Point: 355.9±25.0 °C(Predicted)
• Appearance: /
• Density: 1.276±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 4.03±0.20(Predicted)
• CAS DataBase Reference: (1S,3S,5S)-2-(TERT-BUTOXYCARBONYL)-2-AZABICYCLO[3.1.0]HEXANE-3-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,3S,5S)-2-(TERT-BUTOXYCARBONYL)-2-AZABICYCLO[3.1.0]HEXANE-3-CARBOXYLIC ACID(197142-36-2)
• EPA Substance Registry System: (1S,3S,5S)-2-(TERT-BUTOXYCARBONYL)-2-AZABICYCLO[3.1.0]HEXANE-3-CARBOXYLIC ACID(197142-36-2)

Safety Data

• Hazardous Substances Data: 197142-36-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(1S,3S,5S)-2-(TERT-BUTOXYCARBONYL)-2-AZABICYCLO[3.1.0]HEXANE-3-CARBOXYLIC ACID is used as an impurity in the development and production of Saxagliptin (S143500). Saxagliptin is a potent and selective reversible inhibitor of dipeptidyl peptidase-4, a drug being developed for the treatment of type 2 diabetes. The presence of (1S,3S,5S)-2-(TERT-BUTOXYCARBONYL)-2-AZABICYCLO[3.1.0]HEXANE-3-CARBOXYLIC ACID as an impurity is significant because it can impact the efficacy, safety, and overall quality of the final drug product.
Application Reason:
The importance of (1S,3S,5S)-2-(TERT-BUTOXYCARBONYL)-2-AZABICYCLO[3.1.0]HEXANE-3-CARBOXYLIC ACID lies in its role as an impurity in the synthesis of Saxagliptin. Controlling and understanding the presence of (1S,3S,5S)-2-(TERT-BUTOXYCARBONYL)-2-AZABICYCLO[3.1.0]HEXANE-3-CARBOXYLIC ACID is crucial for ensuring the safety and effectiveness of the drug. It is rapidly absorbed after oral administration and contributes to the pharmacokinetic profile of Saxagliptin, which is compatible with once daily dosing. This makes it a valuable compound to study and monitor in the context of pharmaceutical development and drug delivery systems.

Upstream product

• 1208008-34-7 (3S)-3-((tert-butyldiphenylsilyloxy)methyl)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane 
• 194594-23-5 5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 501096-37-3 (S)-di-tert-butyl 2,3-dihydro-1H-pyrrole-1,2-dicarboxylate 
• 228579-90-6 tert-butyl (2S)-(1-tert-butoxycarbonyl)-5-hydroxypyrrolidine-2-carboxylate 
• 7149-65-7 ethyl (S)-pyroglutamate 
• 178172-26-4 (5S)-4,5-dihydro-1H-pyrrol-1,5-dicarboxylic acid [1-(1,1-dimethylethyl)] 5-ethyl ester 
• 144978-35-8 (S)-ethyl N-tert-butoxycarbonylpyroglutamate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 98-79-3 L-Pyroglutamic acid 
• 214193-13-2 cis-4,5-methano-L-proline 
• 1313751-21-1 C₂₁H₃₄N₂O₇ 
• 361440-67-7 [1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester 
• 214193-11-0 (1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-formic acid ethyl ester 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 361442-01-5 tert-butyl [(1S)-2-[(1S,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hex-2-yl]-1-(3-hydroxytricyclo[3.3.1.1³'⁷]dec-1-yl)-2-oxoethyl]carbamate 
• 1097133-53-3 (1S,3S,5S)-2-[(R)-2-(3-chlorophenyl)-2-hydroxyacetyl]-2-azabicyclo[3.1.0]hexane-3-carboxylic acid 5-chloro-2-tetrazol-1-ylbenzylamide 
• 1097134-10-5 (1S,3S,5S)-N-[[5-chloro-2-(tetrazol-1-yl)phenyl]methyl]-4-[(2R)-2-hydroxy-3-pyrazol-1-ylpropanoyl]-4-azabicyclo[3.1.0]hexane-3-carboxamide 
• 1097133-50-0 (1S,3S,5S)-2-((R)-2-hydroxy-3-pyridin-2-ylpropionyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid 5-chloro-2-tetrazol-1-ylbenzylamide 
• 1097133-52-2 (1S,3S,5S)-2-(2-hydroxy-3-methoxy-3-methylbutyryl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid 5-chloro-2-tetrazol-1-ylbenzylamide 
• 1097133-26-0 (1S,3S,5S)-2-((R)-3-cyclopropyl-2-hydroxypropionyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid 5-chloro-2-tetrazol-1-ylbenzylamide 
• 1097133-17-9 (1S,3S,5S)-2-((R)-2-hydroxy-4,4-dimethylpentanoyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid 5-chloro-2-tetrazol-1-ylbenzylamide 
• 1097133-01-1 (1S,3S,5S)-2-((R)-2-hydroxy-2-phenylacetyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid 5-chloro-2-tetrazol-1-ylbenzylamide 
• 1097133-07-7 (1S,3S,5S)-2-((R)-2-hydroxy-3,3-dimethylbutyryl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid 5-chloro-2-tetrazol-1-ylbenzylamide 
• 1097263-88-1 (1S,3S,5S)-2-aza-bicyclo[3.1.0]hexane-3-carboxylic acid 5-chloro-2-tetrazol-1-yl-benzylamide 
• 1097134-20-7 (1S,3S,5S)-3-(5-chloro-2-tetrazol-1-yl-benzylcarbamoyl)-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester 
• 361440-69-9 (2S,4S,5S)-4,5-methano-L-proline carboxylamide trifluoroacetate 
• 361440-67-7 [1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester 

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