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

Participants

Reaction Conditions

Reaction Steps

1-Methylimidazole (0.53 ml, 6.7 mmol) was added into a solution of (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-1-{[(phenylmethyl)oxy]carbonyl}-3-pyrazolidinecarboxylic acid (1.2 g, 2.23 mmol) in N,N-dimethylformamide (DMF) (15.9 ml). The resulting solution was cooled to 0° C., and then mesyl chloride (0.18 ml, 2.34 mmol) was added dropwise at 0° C. Then 4-pyrimidinamine (0.255 g, 2.68 mmol) was added, and the reaction mixture was stirred for 1 h at room temperature. The reaction solution was purified via reverse phase HPLC (Gilson) to yield phenylmethyl (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-3-[(4-pyrimidinylamino)carbonyl]-1-pyrazolidinecarboxylate (1.21 g, 88% yield).

Provenance & Evidence