400720-05-0

Basic information

• Product Name: [1S-, 2R-, 5R-]3-Aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 3-tert-butyl ester
• Synonyms: [1S-, 2R-, 5R-]3-Aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 3-tert-butyl ester;(1S,2S,5R)-3-(TERT-BUTOXYCARBONYL)-3-AZABICYCLO (1S,2S,5R)-3-(TERT-BUTOXYCARBONYL)-3-AZABICYCLO[3.1.0]HEXANE-2-CARBOXYLIC ACID;3-Azabicyclo[3.1.0]hexane-2,3-dicarboxylic acid, 3-(1,1-diMethylethyl) ester, (1S,2S,5R)-;(1R,4S,5S)-3-tert-Butoxycarbonyl-3-azabicyclo[3.1.0]hexane-4-carboxylic acid
• CAS NO: 400720-05-0
• Molecular Formula: C₁₁H₁₇NO₄
• Molecular Weight: 227.25698
• Mol File: 400720-05-0.mol

Chemical Properties

• Melting Point: 263-265 °C(Solv: water (7732-18-5); acetone (67-64-1))
• Boiling Point: 355.9±25.0 °C(Predicted)
• Appearance: /
• Density: 1.276±0.06 g/cm3(Predicted)
• PKA: 4.03±0.20(Predicted)
• CAS DataBase Reference: [1S-, 2R-, 5R-]3-Aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 3-tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: [1S-, 2R-, 5R-]3-Aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 3-tert-butyl ester(400720-05-0)
• EPA Substance Registry System: [1S-, 2R-, 5R-]3-Aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 3-tert-butyl ester(400720-05-0)

Safety Data

• Hazardous Substances Data: 400720-05-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
[1S-, 2R-, 5R-]3-Aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 3-tert-butyl ester is used as a potential pharmaceutical compound for its unique molecular structure and functional groups. The bicyclic ring system and carboxylic acid groups may provide opportunities for the development of new drugs with specific therapeutic properties.
Used in Organic Synthesis:
[1S-, 2R-, 5R-]3-Aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 3-tert-butyl ester is used as a building block or intermediate in organic synthesis. Its complex structure and functional groups can be utilized in the synthesis of other organic compounds, potentially leading to the development of new materials or chemical processes.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 1051393-66-8 (trans)-3-(tert-butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid 
• 1051393-66-8 rac-cis(1S,2R,5R)-3-[(tert-butoxy)carbonyl]-3-azabicyclo[3.1.0]hexane-2-carboxylic acid 

Downstream Products

• 1097132-93-8 (1S,2S,5R)-3-((R)-2-hydroxy-3,3-dimethylbutyryl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid 5-chloro-2-tetrazol-1-ylbenzylamide 
• 1097132-95-0 (1S,2S,5R)-3-((R)-2-hydroxy-2-phenylacetyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid 5-chloro-2-tetrazol-1-ylbenzylamide 
• 1097133-19-1 (1S,2S,5R)-3-((R)-2-hydroxy-4,4-dimethylpentanoyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid 5-chloro-2-tetrazol-1-ylbenzylamide 
• 1097133-36-2 (1S,2S,5R)-3-((R)-2-hydroxy-3-phenylpropionyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid 5-chloro-2-tetrazol-1-yl-benzylamide 
• 1097133-32-8 (1S,2S,5R)-3-((R)-2-cyclohexyl-2-hydroxyacetyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid 5-chloro-2-tetrazol-1-ylbenzylamide 
• 1097133-21-5 (1S,2S,5R)-3-((R)-3-cyclopropyl-2-hydroxypropionyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid 5-chloro-2-tetrazol-1-ylbenzylamide 
• 1097133-34-0 (1S,2S,5R)-3-((R)-3-tert-butoxy-2-hydroxypropionyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid 5-chloro-2-tetrazol-1-ylbenzylamide 
• 1097134-11-6 (1R,4S,5S)-N-[[5-chloro-2-(tetrazol-1-yl)phenyl]methyl]-3-[(2R)-2-hydroxy-3-pyrazol-1-ylpropanoyl]-3-azabicyclo[3.1.0]hexane-4-carboxamide 

Relevant articles and documents

Synthesis of all four stereoisomers of 3-(tert-butoxycarbonyl)-3- azabicyclo[3.1.0]hexane-2-carboxylic acid

A synthesis of all four stereoisomers of 3-(tert-butoxycarbonyl)-3- azabicyclo[3.1.0]hexane-2-carboxylic acid has been developed, thereby significantly shortening the known literature procedures for the syntheses of these unnatural amino acids. With a simple adjustment of the reaction conditions, we were able to obtain either pure cis or trans acid. Optical resolution was accomplished via diastereomeric salt formation or alternatively via chromatography on a chiral stationary phase. Finally, ab initio calculations gave an explanation for the observed cis selectivity in the initial step.

Discovery of highly potent and selective α4β2-nicotinic acetylcholine receptor (nAChR) partial agonists containing an isoxazolylpyridine ether scaffold that demonstrate antidepressant-like activity. Part II

In our continued efforts to develop α4β2-nicotinic acetylcholine receptor (nAChR) partial agonists as novel antidepressants having a unique mechanism of action, structure-activity relationship (SAR) exploration of certain isoxazolylpyridine ethers is presented. In particular, modifications to both the azetidine ring present in the starting structure 4 and its metabolically liable hydroxyl side chain substituent have been explored to improve compound druggability. The pharmacological characterization of all new compounds has been carried out using [3H]epibatidine binding studies together with functional assays based on 86Rb+ ion flux measurements. We found that the deletion of the metabolically liable hydroxyl group or its replacement by a fluoromethyl group not only maintained potency and selectivity but also resulted in compounds showing antidepressant-like properties in the mouse forced swim test. These isoxazolylpyridine ethers appear to represent promising lead candidates in the design of innovative chemical tools containing reporter groups for imaging purposes and of possible therapeutics.