Water → HCID 178497942, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-[4-(adamantan-1-yloxy)-3-oxo-butyrylamino]-benzoic acid methyl ester (9.95 g, 25.8 mmol) in acetic acid (100 mL) and THF (90 mL) was added water (12 mL). The mixture was cooled to 5° C. and an aqueous solution (16 mL) of sodium nitrite (2.31 g, 35.0 mmol) was added dropwise while maintaining the temperature below 10° C. Upon completion of the addition, the reaction mixture was allowed to warm to room temperature and stirred for 1 h. The solvent was removed under reduced pressure and the residue was partitioned between saturated aqueous NaHCO3 and ethyl acetate. The aqueous phase was discarded and the organic phase was washed with further saturated aqueous NaHCO3 and brine. The organic phase was dried (MgSO4) and the solvent was evaporated at reduced pressure to afford the title product as a yellow foam (10.15 g, 95%). 1H NMR (CDCl3) 11.06 (1H, br s), 8.25 (1H, s), 7.93-7.90 (1H, m), 7.84-7.81 (1H, m), 7.51-7.41 (1H, m), 4.83 (2H, s), 3.95 (3H, s), 2.20 (3H, s), 1.82-1.57 (12H, m).

Provenance & Evidence