Potassium Carbonate → HCID 178447082, compound

Participants

Reaction Steps

In an analogous manner to that described in Example 4 by cleaving off the Boc protecting group from (S)-N-[(1S, 2RS)-1-(cyclohexylmethyl)-2-hydroxy-3-nitropropyl]-α-[(R)-α-(3,3-dimethyl-2-oxobutyl)hydrocinnamamido]-3-t-butoxycarbonylimidazole-4-propionamide with potassium carbonate in methanol and subsequently purifying by chromatography on 50 g of silica gel using a 200:10:1 mixture of methylene chloride, methanol and ammonia as the eluting agent there were obtained the two epimeric compounds (S)-N-[(1S,2S or R)-1-(cyclohexylmethyl)-2-hydroxy-3-nitropropyl]-α-[(R)-α-(3 3-dimethyl-2-oxobutyl)hydrocinnamamido]imidazole-4-propionamide and (S)-N[(1S,2R or S)-1-(cyclohexylmethyl)-2-hydroxy-3-nitropropyl]-α-[(R)-α-(3.3-dimethyl-2-oxobutyl)hydrocinnamamido]imidazole-4-propionamide, in both cases as a foam, MS (each): 584 (M+H)+.

Provenance & Evidence