Sodium Hydroxide → 2-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-(prop-2-en-1-yloxy)piperidin-1-yl]-4-(1-methyl-1H-1,2,4-triazol-5-yl)-1,3-thiazole-5-carboxylic acid

Participants

Reaction Steps

A solution of methyl 2-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-(prop-2-en-1-yloxy)piperidin-1-yl]-4-(1-methyl-1H-1,2,4-triazol-5-yl)-1,3-thiazole-5-carboxylate (Example 30, 90 mg, 0.162 mmol) and 2N sodium hydroxide (4 mL) in methanol (30 mL) was stirred at room temperature for 4 h. The reaction mixture was concentrated under reduced pressure and the resulting residue was dissolved in water, which was acidified to pH 3 with 2 N hydrochloric acid (2 mL). The resulting solid was collected by filtration and dried to afford 2-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-(prop-2-en-1-yloxy)piperidin-1-yl]-4-(1-methyl-1H-1,2,4-triazol-5-yl)-1,3-thiazole-5-carboxylic acid (40 mg, 72%) as solid.

Provenance & Evidence