tert-Butyl methylsulfonyl{3-[(2S)oxiranylmethoxy]phenyl}carbamate → tert-butyl 3-{[(2S)-3-({4-[(1-{[(4-fluorobenzyl)amino]carbonyl}-4-piperidinyl)amino]phenethyl}amino)-2-hydroxypropyl]oxy}phenyl(methylsulfonyl)carbamate

Participants

Reaction Steps

4-[4-(2-Aminoethyl)anilino]-N-(4-fluorobenzyl)-1-piperidinecarboxamide formate (0.591 g, 1.42 mmol) was reacted with tert-butyl methylsulfonyl{3-[(2S)oxiranylmethoxy]phenyl]carbamate (0.488 g, 1.42 mmol) according to Procedure G (eluant: 20:1 going to 10:1 chloroform-methanol) to give tert-butyl 3-{[(2S)-3-({4-[(1-{[(4-fluorobenzyl)amino]carbonyl}-4-piperidinyl)amino]phenethyl}amino)-2-hydroxypropyl]oxy}phenyl(methylsulfonyl)carbamate which was dissolved in formic acid and stirred at ambient temperature overnight. The solvent was removed in vacuo and the residue purified by flash chromatography on silica gel Merck-60 (eluant: 5:1 chloroform-methanol) to furnish the title compound (0.1 g, 0.163 mmol).

Provenance & Evidence