cas 868071-17-4, (3S)-2',4',5'-Trifluoro-3-hydroxybenzenebutanoic acid

Articles about 868071-17-4Total 10 be found

A novel synthesis of (2S)-3-(2,4,5-trifluorophenyl)propane-1,2-diol by sharpless asymmetric epoxidation method
Synthesis of (2S)-3-(2,4,5-trifluorophenyl)propane-1,2-diol by the Sharpless asymmetric epoxidation reaction has been achieved. 2,4,5-Trifluorobenzaldehyde with methyl 2-(triphenyl-λ5-phosphanylidene)acetate gave methyl (E)-3-(2,4,5-trifluorophenyl)acrylate in 83% yield. The reduction of ester group with DibalH followed by Sharpless asymmetric epoxidation gave ((2R,3R)-3-(2,4,5-trifluorophenyl)oxiran-2-yl)methanol. Pd/C-catalyzed hydrogenation of epoxy alcohol furnished (2S)-3-(2,4,5-trifluorophenyl)propane-1,2-diol with >90% ee and 71% yield.
Anil, Derya,Altundas, Ramazan,Kara, Yunus
p. 852 - 858
(2019/03/23)

Preparation method of sitagliptin intermediate
The invention discloses a preparation method of a sitagliptin intermediate, which comprises the following steps: carrying out asymmetric Aldol reaction of raw materials 2,4,5-trifluoro-phenylacetaldehyde and acetone under the induced catalysis of L-proline, and then carrying out hydroxyl group protection, Baeyer-Villiger reaction, deprotection and esterolysis to obtain the intermediate VI. The preparation method has the following advantages: the raw materials are cheap and readily available, the cost is low, few synthesis steps are involved, the reaction condition is mild, the method is environment-friendly, the stereoselectivity is high, and the method can be used for industrial production.
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Paragraph 061-0062

(2017/09/01)

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.
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Paragraph 0161; 0162; 0163; 0164

(2013/06/28)

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.
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(2012/03/26)

PROCESSES FOR THE PREPARATION OF R-SITAGLIPTIN AND INTERMEDIATES THEREOF
The present invention relates to the synthesis of R-sitagliptin. The present invention also relates to a compound of formula (IV) or its salt, that are useful as key intermediate in the synthesis of R-sitagliptin or pharmaceutically acceptable salts thereof.
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(2012/04/17)

Novel and enantioselective syntheses of (R)- and (S)-3-hydroxy-4-(2,4,5- trifluorophenyl)butanoic acid: A synthon for sitagliptin and its derivatives
A new synthetic strategy for (R)- and (S)-3-hydroxy-4-(2,4,5- trifluorophenyl)butanoic acid, a building block in the preparation of sitagliptin and its derivatives, was developed. Pd(OAc)2 catalyzed coupling of 2,4,5-trifluoro-1-iodobenzene wit
Fistikci, Meryem,Gundogdu, Ozlem,Aktas, Derya,Secen, Hasan,Sahin, M. Fethi,Altundas, Ramazan,Kara, Yunus
p. 2607 - 2610
(2012/05/20)

Process for the synthesis of beta-amino acids and derivatives thereof
The present invention relates to a process for the preparation of β-amino acids and derivatives thereof, which is especially suited for gliptins and particularly sitagliptin. A key step makes use of suitably derivatized epoxides or aziridines, which owing to a chirality provides a source of chirality for intermediates which are suitable for building up β-amino acids and similar compounds, in particular in the construction of the sitagliptin molecule.
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Page/Page column 29

(2012/01/06)

METHOD FOR PREPARING INTERMEDIATE OF SITAGLIPTIN USING CHIRAL OXIRANE
Disclosed is: a novel, simple and low-cost method for preparing 3-hydroxy-4-(2,4,5-trifluorophenyl)-butyric acid, particularly (3S)-3-hydroxy-4-(2,4,5-trifluorophenyl)-butyric acid, which is used as a key intermediate in the preparation of sitagliptin.
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(2011/04/25)

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.
Zhu, Yanyun,Xia, Shuang,Zhu, Mingjie,Yi, Weiyin,Cheng, Jiagao,Song, Gonghua,Li, Zhong,Lu, Peng
experimental part
p. 4953 - 4962
(2010/11/18)

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.
Hansen, Karl B.,Balsells, Jaume,Dreher, Spencer,Hsiao, Yi,Kubryk, Michele,Palucki, Michael,Rivera, Nelo,Steinhuebel, Dietrich,Armstrong III, Joseph D.,Askin, David,Grabowski, Edward J. J.
p. 634 - 639
(2012/12/25)