1-Methylimidazole → HCID 86706369, compound

Participants

Reaction Conditions

Reaction Steps

1-Methylimidazole (178 μl, 2.232 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 (400 mg, 0.744 mmol) in DCM (4.08 ml). The resulting solution was cooled to 0° C., and then mesyl chloride (60.5 μl, 0.781 mmol) was added dropwise at 0° C. To the reaction mixture was added 2-[(dimethylamino)methyl]-4-pyrimidinamine (147 mg, 0.967 mmol) in 1 ml of DCM. After stirring for 1.5 hrs at ambient temperature, the solvent was removed under reduced pressure to give a residue which was purified by RP-HPLC to yield phenylmethyl (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-3[({2-[(dimethylamino) methyl]-4-pyrimidinyl}amino)carbonyl]-1-pyrazolidine carboxylate (104 mg, 0.147 mmol, 20% yield). MS (ES+) m/z 672.2 (MH+).

Provenance & Evidence