Sodium Hydroxide → HCID 68486860, compound

Participants

Reaction Conditions

Reaction Steps

A Parr hydrogenation shake flask is charged with [(3S)-3-(hydroxymethyl)-6-nitro-2,3-dihydro-1,4-benzodioxin-5-yl]acetic acid (20.00 g, 74.2 mmol), NaOH (0.33 N, 300 mL, 99 mmol) and palladium (10% on carbon, 1.6 g). The vessel is pressurized to 50 psi with hydrogen and shaken for 3 h, at which point the pressure is released and the mixture is filtered through celite. The solution is acidified with concentrated. HCl (20 mL) and heated to 65° C. for 7 h. The heating is discontinued, and the suspension is stirred overnight. The precipitate is collected by vacuum filtration, and the filter cake is washed with water (50 mL) and dried under suction to give the title compound (13.81 g, 84%) as a tan powder. LCMS (Standard Method): 1.81 min, 222 (M+H)+. 1NMR (300 MHz, DMSO-d6) δ 10.17 (br s, 1H), 6.66 (d, J=8.2 Hz, 1H), 6.27 (d, J=8.2, 1H), 5.03 (br s, 1H), 4.25-4.13 (m, 2H), 3.98-3.91 (m, 1H), 3.65-3.57 (m, 2H), 3.31 (br s, 4H).

Provenance & Evidence