saxagliptin

Base Information

• Chemical Name: saxagliptin
• CAS No.: 1564265-93-5
• Molecular Formula: C₁₈H₂₅N₃O₂
• Molecular Weight: 315.415
• Mol file: 1564265-93-5.mol

Synonyms:

Chemical Property of saxagliptin

Chemical Property:

• Boiling Point: 548.7±35.0 °C(Predicted)
• PKA: 15.12±0.40(Predicted)
• Density: 1.35±0.1 g/cm3(Predicted)

Purity/Quality:

99% ^*data from raw suppliers

(2’R,2S,cis)-Saxagliptin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (2’R,2S,cis)-Saxagliptin is an impurity of Saxagliptin (S143500); a potent and selective reversible inhibitor of dipeptidyl peptidase-4 (DPP-IV) developed for the treatment of type 2 diabetes.

Technology Process of saxagliptin

There total 126 articles about saxagliptin 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: 85.0%

(R)-N-Boc-3-hydroxyadamantylglycine-L-trans-4,5-methanoprolinenitrile (1564267-08-8) → (R)-3-hydroxyadamantylglycine-L-trans-4,5-methanoprolinenitrile (1564265-98-0,1564265-93-5)

Guidance literature:

With hydrogenchloride; In water; isopropyl alcohol; at 65 ℃; for 1.5h;

DOI:10.1016/j.bmc.2013.12.061

Reference yield:

saxaglipitin → (1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-1-oxoethyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile (361442-04-8,1564265-93-5)

Guidance literature:

With sodium hydroxide; In dichloromethane; water; at 20 ℃; for 1h; pH=9;

Reference yield:

[(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 → (1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-1-oxoethyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile (361442-04-8,1564265-93-5)

Guidance literature:

[(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; With hydrogenchloride; water; In methanol; dichloromethane; at 0 - 20 ℃; for 20.6667h;

With sodium hydroxide; In water; pH=> 11;

upstream raw materials:

C₂₂H₂₃F₆N₃O₄

C₂₀H₂₄F₃N₃O₃

saxagliptin monohydrate

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

Downstream raw materials:

5-hydroxy-saxagliptin

Refernces

• 1、 -. "Preparation method of saxagliptin monohydrate crystal form". Paragraph 0038-0074. . Retrieved 2021/08/07.
• 2、 -. "Preparation method of saxagliptin". Paragraph 0010. . Retrieved 2020/06/02.