tert-Butyl {(1S)-1-[(2R)-oxiran-2-yl]-2-phenylethyl}carbamate → 1-[2(S)-hydroxy-3(S)-(tert-butoxycarbonylamino)-4-phenylbutyl]-1-[4-biphenylylmethyl]-2-[tert-butoxycarbonyl)hydrazine

Participants

Reaction Conditions

Reaction Steps

A solution of 58.7 g (197 mmol) of N1 -(tert-butoxycarbonyl)-N2 -(4-biphenylylmethyl)hydrazine and 51.8 g (197 mmol) of N-(tert-butoxycarbonyl)-2(S)-amino-1-phenyl-3(R)-3,4-epoxybutane (=(2R,3S)-1-[3-Boc-amino-2-phenylethyl]-oxirane) in 700 ml of absolute methanol is heated to reflux temperature during 16 h. The mixture is then cooled to 0° C. and diluted with 1.5 l of water. The solid is filtered and dried at 70° C. for 6 h to give the title compound:

Provenance & Evidence