Potassium Carbonate → 1-[2(S)-hydroxy-3(S)-amino-4-phenyl-butyl]-1-[cyclohexylmethyl]-2-[tert-butoxycarbonyl]-hydrazine

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, 2.0 g (4.10 mmol) of 1-[2(S)-hydroxy-3(S)-(trifluoroacetylamino)-4-phenyl-butyl]-1-[cyclohexylmethyl]-2-[tert-butoxycarbonyl]-hydrazine (Example 96b) dissolved in 316 ml of MeOH are heated to 70° C., 103 ml of 1M aqueous K2CO3 solution are added dropwise, and the mixture is stirred for 18 h at 70° C. The reaction mixture is concentrated by evaporation under HV and the residue is partitioned between 3 portions of methylene chloride, 2 portions of water and brine. Concentration by evaporation of the organic phases, which have been dried with Na2SO4, yields the title compound: 1H-NMR (200 MHz, CD3OD): 1.42 (s, 9 H, Boc), 0.8-2.1 (m, 11H, cyclohexyl), 2.35-3.0 (m, 7H), 3.51 (m, 1H), 7.25 (m, 5H).

Provenance & Evidence