Synthesis of a carbon‐14 labeled 1‐(indole‐6‐carbonyl‐ D ‐phenylglycinyl)‐4‐(1‐methylpiperidin‐4‐YL)piperazine‐[carbonyl‐ 14 C], LY517717‐[ 14 C], a factor Xa inhibitor | Zendy

Kuo Fengjiun | Zendy; Clodfelter Dean K. | Zendy; Priest Tamara R. | Zendy; Kau Donald L. K. | Zendy

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Synthesis of a carbon‐14 labeled 1‐(indole‐6‐carbonyl‐ D ‐phenylglycinyl)‐4‐(1‐methylpiperidin‐4‐YL)piperazine‐[carbonyl‐ 14 C], LY517717‐[ 14 C], a factor Xa inhibitor

Author(s) -

Kuo Fengjiun,

Clodfelter Dean K.,

Priest Tamara R.,

Kau Donald L. K.

Publication year - 2004

Publication title -

journal of labelled compounds and radiopharmaceuticals

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.432

H-Index - 47

eISSN - 1099-1344

pISSN - 0362-4803

DOI - 10.1002/jlcr.847

Subject(s) - chemistry , piperazine , benzaldehyde , stereochemistry , strecker amino acid synthesis , moiety , potassium cyanide , cyanide , organic chemistry , enantioselective synthesis , catalysis

Human Factor Xa is a trypsin‐like serine protease, which serves a critical role in blood coagulation events. LY517717 is currently under clinical investigation as a Factor Xa inhibitor. To support the ADME studies, LY517717 was synthesized using D ‐phenylglycine with a carbon‐14 labeled carboxyl moiety. This key component, D ‐phenylglycine‐[carboxyl‐ 14 C], was synthesized by a Strecker synthesis on benzaldehyde with potassium [ 14 C]cyanide, followed by a resolution of DL ‐phenyl‐glycine methyl ester‐[carbonyl‐ 14 C] with (+)‐tartaric acid in the presence of benzaldehyde. Copyright © 2004 John Wiley & Sons, Ltd.

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