767352-29-4

Basic information

• Product Name: (R)-3-(Benzyloxyamino)-4-(2,4,5-trifluorophenyl)butanoic acid
• Synonyms: (R)-3-(BENZYLOXYAMINO)-4-(2,4,5-TRIFLUOROPHENYL)BUTANOIC ACID;(3R)-BenzyloxyaMino-4-(2,4,5-trifluoro-phenyl)-butyric acid;Sitagliptin-Benzyloxy butanoic acid
• CAS NO: 767352-29-4
• Molecular Formula: C₁₇H₁₆F₃NO₃
• Molecular Weight: 339.31
• Mol File: 767352-29-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 456.7 °C at 760 mmHg
• Flash Point: 230 °C
• Appearance: /
• Density: 1.329 g/cm³
• Refractive Index: 1.547
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (R)-3-(Benzyloxyamino)-4-(2,4,5-trifluorophenyl)butanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-(Benzyloxyamino)-4-(2,4,5-trifluorophenyl)butanoic acid(767352-29-4)
• EPA Substance Registry System: (R)-3-(Benzyloxyamino)-4-(2,4,5-trifluorophenyl)butanoic acid(767352-29-4)

Safety Data

• Hazardous Substances Data: 767352-29-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C17H16F3NO3/c18-14-9-16(20)15(19)7-12(14)6-13(8-17(22)23)21-24-10-11-4-2-1-3-5-11/h1-5,7,9,13,21H,6,8,10H2,(H,22,23)/t13-/m1/s1

Upstream product

• 868071-16-3 3(S)-4-(2,4,5-trifluorophenyl)-3-hydroxybenzenebutanoic acid methyl ester 
• 769195-26-8 4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester 
• 75-75-2 methanesulfonic acid 
• 1380521-84-5 tert-butyl (E)-4-(2',4',5'-trifluorophenyl)but-2-enoate 
• 622-33-3 N-benzyloxyamine 
• 1447614-14-3 (R)-3-((benzyloxy)amino)-4-(2,4,5-trifluorophenyl)butanoic acid (R)-(+)-N-benzyl-α-methylbenzylamine salt 
• 1260029-44-4 (E)-4-(2,4,5-trifluoro-phenyl)-but-2-enoic acid methyl ester 
• 1402569-80-5 methyl 3-(benzyloxyamino)-4-(2,4,5-trifluorophenyl) butanoate 
• 767352-30-7 N-(benzyloxy)-4(R)-[1-methyl-(2,4,5-trifluorophenyl)]-2-oxoazetidine 

Downstream Products

• 1256815-23-2 (3R)-3-(benzyloxyamino)-1-[hexahydro-3-oxo-oxazolo[3,4-a]pyrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)butan-1-one 
• 1256815-24-3 (3R)-3-(benzyloxyamino)-1-[hexahydro-3-oxoimidazo[1,5-a]pyrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)butan-1-one 
• 936630-57-8 (R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid 
• 1256815-27-6 (3R)-3-(benzyloxyamino)-1-[2-benzyl-hexahydro-3-oxoimidazo[1,5-a]pyrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)butan-1-one 
• 1256815-25-4 (3R)-3-(benzyloxyamino)-1-[2-methyl-hexahydro-3-oxoimidazo[1,5-a]pyrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)butan-1-one 
• 1256815-26-5 (3R)-3-(benzyloxyamino)-1-[2-ethyl-hexahydro-3-oxoimidazo[1,5-a]pyrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)butan-1-one 
• 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 
• 486460-32-6 sitagliptin 
• 654671-78-0 sitagliptin phosphate 
• 486460-23-5 (R)-tert-butyl 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-ylcarbamate 

Relevant articles and documents

Preparation method of sitagliptin phosphate

The invention discloses a preparation method of sitagliptin phosphate. The preparation method comprises the following steps: taking 4-(2, 4, 5-trifluorophenyl)-3-methyl oxobutyrate I as a raw material; the reaction is mainly divided into five steps: carrying out asymmetric reduction on the raw material I through an N-heterocyclic carbene palladium catalyst to obtain chiral alcohol ester s-4-(2, 4,5-trifluorophenyl)-3-methyl hydroxybutyrate II; carrying out intramolecular condensation cyclization on the II to obtain chiral lactam quaternary ring (R)-N-benzyloxy-4-[1-methyl-(2, 4, 5-trifluorophenyl)]-2-azetidinone III; carrying out ring opening on the III under an alkaline condition to obtain IV; performing condensation reaction to form amide to obtain V; carrying out catalytic reduction onthe V through recycled N-heterocyclic carbene palladium to remove benzyloxy and form phosphate to obtain sitagliptin phosphate VI, wherein the N-heterocyclic carbene palladium catalyst is Pd (IPr-NHC) (acac) Cl or Pd (IPr-NHC) (acac) Oac or Pd (IPr-NHC) (dba) Cl or Pd (IPr-NHC) (dba) OAc; the catalyst is cheap and easily available, can be recycled, and is beneficial to batch production.

PREPARATION OF OPTICALLY PURE ?-AMINO ACID TYPE ACTIVE PHARMACEUTICAL INGREDIENTS AND INTERMEDIATES THEREOF

The present invention relates to the preparation of optically resolved chiral compounds of β-amino acid type active pharmaceutical ingredients (API), more specifically to β-aminobutyryl substituted compounds and especially β-aminobutyryl compounds having γ-bound aryl groups. The present invention more particularly relates to the preparation of enantiomerically enriched chiral compounds useful as intermediates for the preparation of anti-diabetic agents, preferably sitagliptin.

Synthesis, biological assay in vitro and molecular docking studies of new imidazopyrazinone derivatives as potential dipeptidyl peptidase IV inhibitors

A series of novel imidazopyrazinone derivatives were synthesized and evaluated with regard to their ability to inhibit dipeptidyl peptidase IV (DPP-IV) in vitro. Of these compounds (2R)-4-oxo-4-[2-(3-carbamoylbenzyl)- hexahydro-3-oxoimidazo [1,5-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan- 2-amine fumaric acid (17h, IC50 = 78 nM) was shown to effectively inhibit the activity of the dipeptidyl peptidase IV enzyme. Molecular docking studies were also performed to illustrate the binding mode of compounds 15c and 17h. Favorable interactions were identified from the binding of inhibitor 15c with DPP-IV. By analogy to the binding mode of compound 15c, it seems that the introduction of a substituted benzyl moiety onto the imidazopyrazinone could remarkably improve the inhibitory activity of compound 17h.