Sodium Hydroxide → HCID 10300477, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of N-[(2-chloro-6-methylphenyl)carbonyl]-4-(1,3-diethyl-6-methyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine methyl ester (0.82 mmol, 420 mg) in ethanol (2 mL) was added aqueous 1.0 N sodium hydroxide (1.6 mL) at room temperature. The mixture was heated to 50° C. and the resulting clear solution was stirred for 2 h. The ethanol was removed under reduced pressure and the residue was diluted with water (25 mL) and NaOH (3 mL, 1.0N) to dissolve the sodium salt. The aqueous solution was washed with diethyl ether (30 mL) to remove any neutral impurities. The aqueous layer was acidified with 1.0 N HCl and the product was extracted into ethyl acetate (2×25mL). The combined organic extracts were washed with brine solution (50 mL) and were dried over anhydrous magnesium sulfate. Filtration of the drying agent and concentration of the filtrate afforded 277 mg (68% yield) of N-[(2-chloro-6-methylphenyl)carbonyl]-4-(1,3-diethyl-6-methyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine as an amorphous white solid. ES-HRMS m/e calcd for C26H28ClN3O5 (M+Na) 520.1611, found 520.1616.

Provenance & Evidence