Potassium Hydroxide → 2-(3-tert-Butoxycarbonylaminopropoxy)-4-(morpholin-4-yl)benzoic Acid

Participants

Reaction Conditions

Reaction Steps

The methyl 2-[3-(tert-butoxycarbonylamino)propoxy]-4-(morpholin-4-yl)benzoate (2.34 g, 5.93 mmol) was diluted with ethanol (60 mL) and water (60 mL). Potassium hydroxide pellets (1.64 g, 29.2 mmol) were added and the resulting mixture was heated to 70° C. After 2 hours, the reaction was concentrated in vacuo. The residue was diluted with methylene chloride (200 mL) and extracted with saturated aqueous citric acid (2×50 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated to give the desired product (2.24 g, 5.90 mmol, 99%). 1NMR (300 MHz, DMSO-d6): δ 7.59 (d, J=8.7 Hz, 1H); 6.85 (m, 1H); 6.49 (m, 2H); 4.00 (t, J=5.9 Hz, 2H); 3.68 (m, 4H); 3.21 (m, 4H); 3.07 (m, 2H); 1.79 (t, J=6.2 Hz, 2H); 1.33 (s, 9H). IS-MS m/e: 381.4 (m+1).

Provenance & Evidence