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.

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Bibliographic Details
Published in:Tetrahedron letters 2013-12, Vol.54 (50), p.6807-6809
Main Authors: Pan, Xianhua, Li, Xiaojun, Lu, Qingling, Yu, Wansheng, Li, Weijin, Zhang, Qunhui, Deng, Fei, Liu, Feng
Format: Article
Language:English
Subjects:
Aziridine
Bromides
Chemical reactions
Derivatives
Grignard reaction
Inhibitors
Phosphates
Sitagliptin phosphate
Synthesis
Synthesis (chemistry)
Tetrahedrons
β-Amino acid
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Summary: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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2013.09.136