✦ LIBER ✦

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

✍ Scribed by Yoshio Ito; Tetsuhide Kamijo; Hiromu Harada; Fuyuhiko Matsuda; Shire Terashima

Book ID: 104226699
Publisher: Elsevier Science
Year: 1990
Tongue: French
Weight: 323 KB
Volume: 31
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)94685-9

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✦ Synopsis

Optically pure (R)-(l-naphthyhnethyl)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)-( lnaphthylmethyl)succinate with morpholine followed by coupling with methyl (S)-histidinate readily produced the title key synthetic intermediate.

-andNotes 1) a) K.

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