tert-Butyl [2-(3-cyano-2-azabicyclo[3.1.0]hexan-2-yl)-1-(3-hydroxytricyclo[3.3.1.1~3,7~]decan-1-yl)-2-oxoethyl]carbamate

Base Information

• Chemical Name: tert-Butyl [2-(3-cyano-2-azabicyclo[3.1.0]hexan-2-yl)-1-(3-hydroxytricyclo[3.3.1.1~3,7~]decan-1-yl)-2-oxoethyl]carbamate
• CAS No.: 709031-43-6
• Molecular Formula: C23H33N3O4
• Molecular Weight: 415.533
• European Community (EC) Number: 687-691-8
• Mol file: 709031-43-6.mol

Synonyms:709031-43-6;tert-Butyl [2-(3-cyano-2-azabicyclo[3.1.0]hexan-2-yl)-1-(3-hydroxytricyclo[3.3.1.1~3,7~]decan-1-yl)-2-oxoethyl]carbamate;tert-butyl N-[2-(3-cyano-2-azabicyclo[3.1.0]hexan-2-yl)-1-(3-hydroxy-1-adamantyl)-2-oxoethyl]carbamate;Boc-Saxagliptin;BCP06845;tert-Butyl ((1S)-2-((1S,3S,5S)-3-cyano-2-azabicyclo(3.1.0)hex-2-yl)-1-(3-hydroxyadamantan-1-yl)-2-oxoethyl)carbamate;tert-butyl ((1S)-2-((1S,3S,5S)-3-cyano-2-azabicyclo[3.1.0]hex-2-yl)-1-(3-hydroxyadamantan-1-yl)-2-oxoethyl)carbamate;tert-Butyl [(1S)-2-[(1S,3S,5S)-3-cyano-2-azabicyclo[3.1.0]hex-2-yl]-1-(3-hydroxyadamantan-1-yl)-2-oxoethyl]carbamate;Saxagliptin Impurity 16 pound>>N-[(1S)-2-[(1S,3S,5S)-3-cyano-2-azabicyclo[3.1.0]hex-2-yl]-1-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-2-oxoethyl]-Carbamic Acid 1,1-Dimethylethyl Ester

Chemical Property of tert-Butyl [2-(3-cyano-2-azabicyclo[3.1.0]hexan-2-yl)-1-(3-hydroxytricyclo[3.3.1.1~3,7~]decan-1-yl)-2-oxoethyl]carbamate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.594
• Boiling Point: 624.716 °C at 760 mmHg
• PKA: 11.45±0.46(Predicted)
• Flash Point: 331.617 °C
• PSA: 106.15000
• Density: 1.292 g/cm³
• LogP: 2.86628
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 415.24710654
• Heavy Atom Count: 30
• Complexity: 810

Purity/Quality:

99.9% ^*data from raw suppliers

Boc-Saxagliptin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(C(=O)N1C(CC2C1C2)C#N)C34CC5CC(C3)CC(C5)(C4)O
• Uses: Boc-Saxagliptin is a Saxagliptin (S143500) impurity, 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 tert-Butyl [2-(3-cyano-2-azabicyclo[3.1.0]hexan-2-yl)-1-(3-hydroxytricyclo[3.3.1.1~3,7~]decan-1-yl)-2-oxoethyl]carbamate

There total 54 articles about tert-Butyl [2-(3-cyano-2-azabicyclo[3.1.0]hexan-2-yl)-1-(3-hydroxytricyclo[3.3.1.1~3,7~]decan-1-yl)-2-oxoethyl]carbamate 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: 97.9%

(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carbonitrile (866083-42-3) + Na(1+)*C17H26NO5(1-) → 3-cyano-(αS)-α-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-β-oxo-(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-2-ethanecarbamic acid 1,1-dimethylethyl ester (709031-43-6)

Guidance literature:

Na⁽¹⁺⁾*C₁₇H₂₆NO₅^(1-); With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; In ethyl acetate; acetonitrile; at 20 ℃; for 5h;

(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carbonitrile; In ethyl acetate; acetonitrile; at 20 ℃; for 2h; Reagent/catalyst;

Reference yield: 92.3%

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 (361442-01-5) → 3-cyano-(αS)-α-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-β-oxo-(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-2-ethanecarbamic acid 1,1-dimethylethyl ester (709031-43-6)

Guidance literature:

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; With pyridine; trifluoroacetic anhydride; In tetrahydrofuran; for 1h;

With potassium hydroxide; In methanol; at 20 ℃; for 18h;

DOI:10.1021/jm050261p

Reference yield: 77.0%

(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carbonitrile 4-methylbenzenesulfonate (929106-57-0) + (S)-N-boc-(3-hydroxyadamantan-1-yl)glycine succinimide ester → 3-cyano-(αS)-α-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-β-oxo-(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-2-ethanecarbamic acid 1,1-dimethylethyl ester (709031-43-6)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 20 ℃; for 2h;

upstream 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

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.1^3,7]decane-1-acetic acid

(S)-2-(adamantan-1-yl)-2-(((R)-2-hydroxy-1-phenylethyl)amino)acetonitrile

1-adamantanemethanol

Downstream raw materials:

saxagliptin

Saxagliptin hydrochloride

saxagliptin monohydrate

C₁₈H₂₅N₃O₂*1.33ClH*1.67H₂O

Refernces

• 1、 -. "Method for preparing saxagliptin". Paragraph 0039; 0046; 0048; 0057; 0059; 0062; 0064. . Retrieved 2020/06/16.
• 2、 -. "Novel intermediates for preparing saxagliptin, preparing methods thereof and preparing methods of saxagliptin using the same". Paragraph 0164; 0165. . Retrieved 2017/08/02.