1349649-83-7

Basic information

• Product Name: (R)-2-methyl-N-((R)-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-yl)propane-2-sulfinamide
• Synonyms: (R)-2-methyl-N-((R)-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-yl)propane-2-sulfinamide
• CAS NO: 1349649-83-7
• Molecular Weight: 511.491
• Mol File: 1349649-83-7.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (R)-2-methyl-N-((R)-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-yl)propane-2-sulfinamide(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-methyl-N-((R)-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-yl)propane-2-sulfinamide(1349649-83-7)
• EPA Substance Registry System: (R)-2-methyl-N-((R)-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-yl)propane-2-sulfinamide(1349649-83-7)

Safety Data

• Hazardous Substances Data: 1349649-83-7(Hazardous Substances Data)

Upstream product

• 883267-70-7 2-(2,4,5-trifluorophenyl)ethanol 
• 209995-38-0 (2,4,5-trifluorophenyl)acetic acid 
• 762240-92-6 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride 
• 157911-56-3 2,4,5-trifluorobenzyl bromide 
• 57260-71-6 1-t-Butoxycarbonylpiperazine 
• 327-52-6 1-bromo-2,4,5-trifluorobenzene 
• 1151240-88-8 3-oxo-4-(2,4,5-trifluorophenyl)-butyric acid ethyl ester 
• 486460-21-3 3-trifluoromethyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine 
• 111991-20-9 2-(2,4,5-trifluorophenyl)acetaldehyde 

Downstream Products

• 486460-32-6 sitagliptin 

Relevant articles and documents

A highly stereoselective and efficient synthesis of enantiomerically pure sitagliptin

A highly stereoselective and efficient synthesis of sitagliptin 1 consisting of a chiral β-amino acid unit has been achieved through 6 steps from commercially available 2,4,5-trifluorobenzaldehyde 4. The chiral antidiabetic drug was obtained with almost perfect enantiomeric purity (>99.9% ee) in 40.9% overall yield. The key feature of the synthesis is the addition of a malonate enolate to a chiral sulfinylimine in more than 99:1 dr. Our synthetic procedure proved to be highly efficient, economical, and sustainable.

Sitagliptin synthesis method

The invention discloses a sitagliptin synthesis method, which comprises: carrying out a reaction on a compound represented by a formula IV, (R)-(+)-tert-butyl sulfinamide and hydrogen under the catalysis of a catalyst to obtain a compound represented by a formula V; and carrying out a hydrolysis reaction on the compound represented by the formula V to obtain a compound represented by a formula VI,ie., sitagliptin. According to the present invention, the method has advantages of easily available raw materials, simple steps, high yield and mild reaction conditions, and is suitable for industrial production. The formulas IV, V and VI are defined in the specification.

A method for synthesizing row sandbank west he

The invention discloses a synthetic method for sitagliptin. The method comprises the following steps that: 2,4,5-trifluorobenzaldehyde is used as a starting raw material and undergoes the Wittig reaction and hydrolysis with hydrochloric acid so as to obtain 2-(2,4,5-trifluorophenyl)acetaldehyde; 2-(2,4,5-trifluorophenyl)acetaldehyde and (R)-(+)-t-butyl sulfenamide are subjected to condensation so as to obtain corresponding acetal; acetal and ethyl bromoacetate undergo the Reformatsky reaction, and then an obtained product undergoes hydrolysis so as to obtain organic acid; the organic acid and 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride are subjected to condensation so as to obtain acetal of t-butyl sulfenamide of sitagliptin; and finally methanol hydrochloride is used for deprotection so as to obtain sitagliptin. The invention has the following advantages: yield in each step is high, operation is simple, reagents used in the method are conventional reagents, usage of an expensive chiral catalyst is avoided, and good industrial prospect is obtained.