2-{[(Tert-butoxy)carbonyl]amino}-3-(pyridin-4-yl)propanoic acid → alpha-amino-N-[(1S,2R,3 S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]-3-(pyridin-4-yl)propionamide

Participants

Reaction Steps

In an analogous manner to that described above, by the condensation of N-(tert-butoxycarbonyl)-3-(pyridin-4-yl)-D,L-alanine [J. Gen. Chem. USSR, 40, 2488 (1970)]and (1S,2R,3S)-3-amino-4-cyclohexyl-1-cyclopropyl-1,2-butanediol followed by acidic hydrolysis there were obtained (S or R)-α-amino-N-[(1S,2R,3 S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]-3-(pyridin-4-yl)propionamide, MS: 267 (M+H)+, and (R or S)-α-amino-N-[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]-3-(pyridin-4-yl)propionamide, MS: 267 (M+H)+, each as a colourless foam.

Provenance & Evidence