Potassium Hydroxide → HCID 68751172, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of ethyl 1-[(2S)-1-{[(benzyloxy)(hydroxy)phosphoryl]oxy}-4-methylpentan-2-yl]-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (Example 23, 330 mg, 0.41 mmol) in ethanol (20 mL) was added 10% potassium hydroxide (69 mg, 1.23 mmol). The reaction mixture was heated to 60-65° C. overnight. The reaction mixture was cooled and then washed with ethyl acetate (20 mL). The pH of the aqueous layer was adjusted to 4 with dilute hydrochloric acid (2N) solution to give a solid precipitate which was filtered and dried to afford 120 mg (30%) of 1-[(2S)-1-{[(benzyloxy)(hydroxy)phosphoryl]oxy}-4-methylpentan-2-yl]-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid.

Provenance & Evidence