1-Methylimidazole → phenylmethyl (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-3-[({2-[(2S)-2,4-dimethyl-1-piperazinyl]-4-pyrimidinyl}amino) carbonyl]-1-pyrazolidinecarboxylate

Participants

Reaction Conditions

Reaction Steps

1-Methylimidazole (133 μl, 1.674 mmol) was added into the solution of (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-1-{[(phenylmethyl)oxy]carbonyl}-3-pyrazolidinecarboxylic acid (300 mg, 0.558 mmol) in dichloromethane (DCM) (4 ml). The resulting solution was cooled to 0° C., and then mesyl chloride (45.4 μl, 0.586 mmol) was added dropwise at 0° C. To the reaction mixture was added 2-[(25)-2,4-dimethyl-1-piperazinyl]-4-pyrimidinamine (127 mg, 0.614 mmol). After stirring for 1 h 40 min at ambient temperature, the reaction solution was purified by RP-HPLC to yield phenylmethyl (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-3-[({2-[(2S)-2,4-dimethyl-1-piperazinyl]-4-pyrimidinyl}amino)carbonyl]-1-pyrazolidinecarboxylate (236 mg, 0.325 mmol, 58% yield). MS (ES+) m/z 515.4 (MH+). MS (ES+) m/z 727.3 (MH+).

Provenance & Evidence