(1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid

Base Information

• Chemical Name: (1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid
• CAS No.: 197142-36-2
• Molecular Formula: C11H17NO4
• Molecular Weight: 227.26
• European Community (EC) Number: 819-598-7
• Mol file: 197142-36-2.mol

Synonyms:197142-36-2;(1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid;(1S,3S,5S)-2-[(tert-butoxy)carbonyl]-2-azabicyclo[3.1.0]hexane-3-carboxylic acid;(1S,3S,5S)-2-[(2-methylpropan-2-yl)oxycarbonyl]-2-azabicyclo[3.1.0]hexane-3-carboxylic acid;(1s,3s,5s)-2-boc-2-azabicyclo[3.1.0]hexane-3-carboxylic acid;(1s,3s,5s)-2-((tert-butoxy)carbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid;SCHEMBL540162;AMY34354;XHA14236;(1S,3S,5S)-2-Boc-2-aza-bicyclo[3.1.0]hexane-3-dicarboxylic acid;AKOS010367750;CS-0053554;EN300-54368;A857649;Z228589610;(1S,3S,5S)-2-(tert-Butoxycarbonyl)-2-azabicyclo-[3.1.0]hexane-3-carboxylic acid;(1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylicacid;(1S,3S,5S)-2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester;2-Azabicyclo[3.1.0]hexane-2,3-dicarboxylic acid, 2-(1,1-dimethylethyl) ester, (1S,3S,5S)-

Chemical Property of (1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid

Chemical Property:

• Boiling Point: 355.9±25.0 °C(Predicted)
• PKA: 4.03±0.20(Predicted)
• PSA: 66.84000
• Density: 1.276±0.06 g/cm3(Predicted)
• LogP: 1.40680
• Storage Temp.: 2-8°C
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 227.11575802
• Heavy Atom Count: 16
• Complexity: 333

Purity/Quality:

98%,99%, ^*data from raw suppliers

(1S,3S,5S)-2-Boc-2-azabicyclo[3.1.0]hexane-3-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1C2CC2CC1C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N1[C@H]2C[C@H]2C[C@H]1C(=O)O
• Uses: (1S,3S,5S)-2-Boc-2-azabicyclo[3.1.0]hexane-3-carboxylic Acid is an impurity of Saxagliptin (S143500), which is a potent and selective reversible inhibitor of dipeptidyl peptidase-4, which is being developed for the treatment of type 2 diabetes. It is absorbed rapidly after oral administration and has a pharmacokinetic profile compatible with once daily dosing.

Technology Process of (1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid

There total 18 articles about (1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid 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%

C21H34N2O7 (1313751-21-1) → (1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid (197142-36-2)

Guidance literature:

C₂₁H₃₄N₂O₇; With sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 16h;

With hydrogenchloride; In water; pH=3;

Reference yield: 96.0%

(1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-formic acid ethyl ester (214193-11-0) → (1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid (197142-36-2)

Guidance literature:

(1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-formic acid ethyl ester; With methanol; lithium hydroxide; water; In tetrahydrofuran; at 20 ℃;

With hydrogenchloride; In tetrahydrofuran; at 20 ℃; for 0.25h; pH=4.5;

Reference yield: 94.0%

di-tert-butyl dicarbonate (24424-99-5) + cis-4,5-methano-L-proline (214193-13-2) → (1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid (197142-36-2)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; water; at 0 - 20 ℃; for 15h;

upstream raw materials:

(S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-5-oxopyrrolidine-1-carboxylate

hydrogenchloride

(1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-formic acid ethyl ester

(3S)-3-((tert-butyldiphenylsilyloxy)methyl)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane

Downstream raw materials:

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

(2S,4S,5S)-4,5-methano-L-proline carboxylamide trifluoroacetate

[1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester

(1S,3S,5S)-3-(5-chloro-2-tetrazol-1-yl-benzylcarbamoyl)-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester

Refernces

• 1、 -. "Method for preparing saxagliptin intermediates". Paragraph 0037; 0083-0088. . Retrieved 2017/08/31.
• 2、 Berger, Gilles,Vilchis-Reyes, Miguel,Hanessian, Stephen. "Structural Properties and Stereochemically Distinct Folding Preferences of 4,5-cis and trans-Methano- L -Proline Oligomers: The Shortest Crystalline PPII-Type Helical Proline-Derived Tetramer". supporting information. p. 13268 - 13272. Retrieved 2015/11/09.