1374966-98-9

Upstream product

• 1404380-75-1 (S)-3-((benzyloxycarbonyl)amino)-4-(2,4,5-trifluorophenyl)-4-oxobutanoic acid methyl ester 
• 40856-59-5 tert-butyl (3S)-2-oxotetrahydrofuran-3-ylcarbamate 
• 1404380-74-0 (S)-3-((benzyloxycarbonyl)amino)-4-(methoxy(methyl)amino)-4-oxobutanoic acid methyl ester 
• 327-52-6 1-bromo-2,4,5-trifluorobenzene 
• 23632-66-8 (4S)-3-benzyloxycarbonyl-4-carboxymethyl-1,3-oxazolidin-5-one 

Downstream Products

• 1204818-19-8 (R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid hydrochloride 
• 1404380-73-9 (S)-benzyl (1,4-dioxo-4-(3-(trifluoromethyl)-5,6,7,8-tetra hydro-[1,2,4]triazolo[4,3-a]pyrazin-7-yl)-1-(2,4,5-trifluorophenyl)butan-2-yl)carbamate 

Relevant academic research and scientific papers

Reaction of (S)-homoserine lactone with Grignard reagents: synthesis of amino-keto-alcohols and β-amino acid derivatives

The ring-opening reaction of homoserine lactone with phenylmagnesium bromides was systematically examined. A reliable method to achieve β-amino acid precursors was developed by tuning the reaction conditions to favor mono-addition to the carbonyl moiety of the lactone.

Manufacturing process for sitagliptin from L-aspartic acid

The present invention relates to a novel manufacturing process of pharmaceutically active compound of formula I used as oral anti-diabetic drug. Starting from L-aspartic acid derivate of formula IV the invention describes preparation of the chiral (R)-β-amino acid of formula II known as a precursor in the synthesis of Sitagliptin (formula I).

A PREPARATION METHOD OF SITAGLIPTIN

The present invention relates to a preparation method of sitagliptin, and more particularly, to a method of preparing sitagliptin using L-aspartic acid having a (R)-beta amino acid structure by mild amide formation, by the use of industrially applicable halo isopropylmagnesium, and by removal of amine protecting group using Pd/C and H2 and carbonyl reduction using reducing agent.