1048703-14-5

Upstream product

• 1380298-39-4 C₁₆H₃₅NO₆SSi 
• 1380298-40-7 C₂₂H₃₉NO₆SSi 
• 1380298-41-8 C₁₅H₃₂BrNO₃Si 
• 191655-45-5 (2S)‐2‐{[(tert‐butoxy)carbonyl]amino}‐4‐[(tert‐butyldimethylsilyl)oxy]butanoic acid 
• 130622-08-1 (2R)-2-tert-butoxycarbonylamino-succinic acid dimethyl ester 
• 397246-14-9 (1-(hydroxymethyl)-3-hydroxypropyl)carbamic acid tert-butyl ester 
• 322691-00-9 2-(tert-butoxycarbonylamino)-butane-1,4-diyl dimethanesulfonate 
• 680993-47-9 1-allyl-2,4,5-trifluorobenzene 
• 1380243-41-3 C₂₄H₂₄F₃NO 
• 1056166-08-5 (2S)-2-(2-hydroxy-ethyl)-aziridine-1-carboxylic acid tert-butyl ester 
• 327-52-6 1-bromo-2,4,5-trifluorobenzene 
• 34619-03-9 tert-butyldicarbonate 
• 1380298-42-9 C₁₂H₂₅NO₇S 
• 915715-25-2 (S)-(3-benzyloxy-1-hydroxymethyl-propyl)-carbamic acid tert-butyl ester 

Downstream Products

• 1048703-15-6 tert-butyl (R)-(4-oxo-1-(2,4,5-trifluorophenyl)butan-2-yl)carbamate 
• 1500076-58-3 (R)-N-(3-amino-4-(2,4,5-trifluorophenyl)butyl)benzamide hydrochloride 
• 1500076-59-4 (R)-N-(3-amino-4-(2,4,5-trifluorophenyl)butyl)-2,3-difluorobenzamide hydrochloride 
• 1500076-60-7 (R)-N-(3-amino-4-(2,4,5-trifluorophenyl)butyl)-4-methoxybenzamide hydrochloride 
• 1500076-61-8 (R)-N-(3-amino-4-(2,4,5-trifluorophenyl)butyl)-4-(methylsulfonyl)-benzamide hydrochloride 
• 1500076-62-9 (R)-N-(3-amino-4-(2,4,5-trifluorophenyl)butyl)-4-sulfamoylbenzamide hydrochloride 
• 1500076-63-0 (R)-N-(3-amino-4-(2,4,5-trifluorophenyl)butyl)-4-(trifluoromethyl)benzamide hydrochloride 
• 1500076-64-1 (R)-N-(3-amino-4-(2,4,5-trifluorophenyl)butyl)-4-(1H-1,2,4-triazol-1-yl)benzamidehydrochloride 
• 1500076-65-2 (R)-N-(3-amino-4-(2,4,5-trifluorophenyl)butyl)-1H-benzo[d]imidazole-6-carboxamide hydrochloride 
• 1500076-66-3 (R)-N-(3-amino-4-(2,4,5-trifluorophenyl)butyl)-1H-benzo[d]-[1,2,3]triazole-6-carboxamide hydrochloride 
• 1500076-67-4 (R)-N-(3-amino-4-(2,4,5-trifluorophenyl)butyl)nicotinamide hydrochloride 
• 1500076-68-5 (R)-N-(3-amino-4-(2,4,5-trifluorophenyl)butyl)thiophene-3-carboxamide hydrochloride 
• 1500076-69-6 (R)-N-(3-amino-4-(2,4,5-trifluorophenyl)butyl)quinoline-6-carboxamide hydrochloride 
• 1500076-70-9 (R)-N-(3-amino-4-(2,4,5-trifluorophenyl)butyl)-2-phenylacetamide hydrochloride 

Relevant academic research and scientific papers

Practical asymmetric synthesis of Sitagliptin phosphate monohydrate

Optically pure sitagliptin phosphate monohydrate is efficiently and practically synthesized through a chiral hemiacetal as the key intermediate in 54% overall yield starting from (E)-4-(2,4,5-trifluorophenyl)but-2-enal and N-boc-protected hydroxylamine. The chiral hemiacetal fragment is constructed by a tandem aza-Michael/hemiacetal reaction catalyzed by an organocatalyst and the influence of acidity of Br?nsted acid on tandem aza-Michael/hemiacetal reaction is researched in detail.

Preparation method of sitagliptin intermediate

The invention discloses a preparation method of a sitagliptin intermediate and belongs to the field of medicine synthesis. The invention provides a preparation method of a compound 2; the compound 2 is prepared without the need of a catalyst and a resolving agent which have a high price and harsh low-temperature conditions, so that the cost is reduced to the great extent; the preparation method has the advantages of simple technology, high purity and high yield and is suitable for mass production.

INTERMEDIATES OF SITAGLIPTIN AND PREPARATION PROCESS THEREOF

Disclosed are intermediates of Sitagliptin, a preparation process thereof, and a process for synthesizing Sitagliptin using these intermediates. Sitagliptin is synthesized by using chiral amino compounds as a raw material, without having to build a chiral center with a chiral asymmetric catalytic hydrogenation, and high-pressure hydrogenation is avoided.

INTERMEDIATES OF SITAGLIPTIN AND PREPARATION PROCESS THEREOF

Disclosed are intermediates of Sitagliptin, a preparation process thereof, and a process for synthesizing Sitagliptin using these intermediates. Sitagliptin is synthesized by using chiral amino compounds as a raw material, without having to build a chiral center with a chiral asymmetric catalytic hydrogenation, and high-pressure hydrogenation is avoided.

Efficient synthesis of sitagliptin phosphate, a novel DPP-IV inhibitor, via a chiral aziridine intermediate

Sitagliptin phosphate, a novel DPP-IV inhibitor of T2DM, has been synthesized via 12 linear steps, in an overall yield of 26%. The key step is the coupling reaction of 2,4,5-trifluorophenylmagnesium bromide with a chiral aziridine derivative, which was prepared from l-homo-serine by simple steps.

Design and synthesis of 4-(2,4,5-Trifluorophenyl)butane-1,3-diamines as dipeptidyl peptidase IV inhibitors

The worldwide prevalence of diabetes has spurred numerous studies on the development of new antidiabetic medicines. As a result, dipeptidyl peptidaseIV (DPP4) has been recognized as a validated target. In our efforts to discover new DPP4 inhibitors, we analyzed the complexed structures of DPP4 available in Protein Data Bank and designed a series of triazole compounds. After enzyme activity assays and crystallographic verification of the binding interaction patterns, we found that the triazole compounds can inhibit DPP4 with micromolar IC50 values. Liver microsome stability and cytochrome P450 metabolic tests were performed on this series, revealing undesirable pharmacokinetic profiles for the triazole compounds. To overcome this liability, we substituted the triazole ring with an amide or urea group to produce a new series of DPP4 inhibitors. Based on its enzyme activity, metabolic stability, and selectivity over DPP8 and DPP9, we selected compound 21r for further study of its invivo effects in mice using an oral glucose tolerance test (OGTT). The results show that 21r has efficacy similar to that of sitagliptin at a dose of 3mgkg-1. The crystal structure of 21r bound to DPP4 also reveals that the trifluoromethyl group is directed toward a subpocket different from the subsite bound by sitagliptin, providing clues for the design of new DPP4 inhibitors.

compounds of formula (I) as serine protease inhibitors

Compounds of formula (I) and compositions thereof and their use as pharmaceutical agents, in particular as inhibitors of serine proteases.