767352-30-7

Usage

Uses

Used in Pharmaceutical Industry:
(4R)-1-(Phenylmethoxy)-4-[(2,4,5-trifluorophenyl)methyl]-2-azetidinone is used as a potential pharmaceutical agent due to its unique structure and the biological activities associated with azetidinones. Its specific stereochemistry and substituents may contribute to its therapeutic effects and selectivity, warranting further investigation for the development of new drugs.

Upstream product

• 209995-38-0 (2,4,5-trifluorophenyl)acetic acid 
• 769195-26-8 4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester 
• 1138326-05-2 (R)-methyl 3-hydroxy-4-(2,4,5-trifluorophenyl)butanoate 
• 868071-17-4 3(S)-4-(2,4,5-trifluorophenyl)-3-hydroxybutanoic acid 
• 622-33-3 N-benzyloxyamine 
• 1176895-65-0 2-(2,4,5-trifluorophenyl)acetyl chloride 

Downstream Products

• 767352-29-4 (R)-3-((benzyloxy)amino)-4-(2,4,5-trifluorophenyl)butanoic acid 
• 654671-78-0 sitagliptin phosphate 
• 486460-32-6 sitagliptin 
• 654671-77-9 sitagliptin phosphate monohydrate 
• 486459-71-6 (2R)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine hydrochloride 
• 1361389-75-4 3(R)-3-[(benzyloxy)amino]-1-[3-(trifluoromethyl)-5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one 

Relevant academic research and scientific papers

Synthesis method of sitagliptin

The invention discloses a synthetic method of sitagliptin. The synthesis method comprises the following steps of: carrying out a reaction on 1,3,5-trifluorophenylacetic acid as a raw material and pivaloyl chloride to convert into acyl chloride; under the

SITAGLIPTIN, SALTS AND POLYMORPHS THEREOF

The present invention relates to an improved process for preparation of Sitagliptin or pharmaceutically acceptable salts thereof. The present invention further relates to novel polymorphs of Sitagliptin salts and process for preparation thereof.

SITAGLIPTIN, SALTS AND POLYMORPHS THEREOF

The present invention relates to an improved process for preparation of Sitagliptin or pharmaceutically acceptable salts thereof. The present invention further relates to novel polymorphs of Sitagliptin salts and process for preparation thereof.

First generation process for the preparation of the DPP-IV inhibitor sitagliptin

A new synthesis of sitagliptin (MK-0431), a DPP-IV inhibitor and potential new treatment for type II diabetes, suitable for the preparation of multi-kilogram quantities is presented. The triazolopyrazine fragment of sitagliptin was prepared in 26% yield over four chemical steps using a synthetic strategy similar to the medicinal chemistry synthesis. Key process developments were made in the first step of this sequence, the addition of hydrazine to chloropyrazine, to ensure its safe operation on a large scale. The beta-amino acid fragment of sitagliptin was prepared by asymmetric reduction of the corresponding beta-ketoester followed by a two-step elaboration to an N-benzyloxy beta-lactam. Hydrolysis of the lactam followed by direct coupling to the triazolopiperazine afforded sitagliptin after cleavage of the N-benzyloxy group and salt formation. The overall yield was 52% over eight steps.