2-Amino-3-methylpyridine → phenylmethyl (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-3-{[(3-methyl-2-pyridinyl)amino]carbonyl}-1-pyrazolidinecarboxylate

Beteiligte Stoffe

Reaktionsschritte

To a solution of 2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-1-{[(phenylmethyl)oxy]carbonyl}-3-pyrazolidine carboxylic acid (as a mixture of diastereomers enriched in (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-1-{[(phenylmethyl)oxy]carbonyl}-3-pyrazolidinecarboxylic acid) (250 mg, 0.465 mmol) in tetrahydrofuran (3 ml) was added N,N-diisopropylethylamine (405 μl, 2.325 mmol) and 2,4,6-trichlorobenzoyl chloride (0.087 mL, 0.558 mmol). The mixture was stirred for 2 h and then the solvent was evaporated. The residue was then diluted with toluene (3 mL). The resulting suspension was treated with 2-amino-3-methylpyridine (61 mg, 0.56 mmol) followed by DMAP (11.3 mg, 0.093 mmol). After 2 h, 15 minutes, the solvent mixture was removed. The residue was diluted with MeOH and purified by reverse-phase HPLC to afford 179 mg (61%) of the title compound as a white solid. LC/MS: (M+H)+: 628.5.

Herkunft & Nachweise