An efficient synthesis of methyl N-[2-(R)-(1-napthylmethyl)-3-(morpholinocarbonyl)propionyl]-(S)-histidinate, the key synthetic intermediate of renin inhibitors

Yoshio Ito, Tetsuhide Kamijo, Hiromu Harada, Fuyuhiko Matsuda, Shire Terashima

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

Optically pure (R)-(1-naphthylmethyl)succinic acid could be efficiently prepared by a combination of optical resolution and racemization of the undesired enantiomer or by catalytic asymmetric reduction of (1-naphthylmethylene)succinic acid over a rhodium (I)-chiral phosphine complex. Highly chemoselective amide formation of di-4-nitrophenyl (R)-(1-naphthylmethyl)succinate with morpholine followed by coupling with methyl (S)-histidinate readily produced the title key synthetic intermediate.

Original languageEnglish
Pages (from-to)2731-2734
Number of pages4
JournalTetrahedron Letters
Volume31
Issue number19
DOIs
Publication statusPublished - Jan 1990
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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