Sodium Hydroxide → HCID 178428888, compound

Participants

Reaction Steps

The crude ethyl 2-(1-hydroxy-6-(5-(N-hydroxycarbamimidoyl)thiazol-2-yloxy)-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate in MeOH/THF (10 mL, 1:1) was added aqueous NaOH solution (200 mg in 3 mL water). After stirring at room temperature for two hours, the reaction mixture was evaporated, acidified with 1N HCl to pH 5 and then concentrated. HPLC purification gave desired product as white solid. 1H NMR (400 MHz, DMSO-d6) δ 10.2 (b, 2H), 9.20 (b, 1H), 7.70 (s, 1H), 7.37 (d, J=2 Hz, 1H), 7.22 (d, J=1.6 Hz, 1H), 5.48 (dd, J=9.2, 2 Hz, 1H), 3.02 (dd, J=15.6, 2.4 Hz, 1H), 2.26 (s, 3H), 2.28 (dd, J=15.6, 9.6 Hz, 1H). 2 protons assumed to be exchanged with solvents. MS (ESI) m/z=364 [M+H]+.

Provenance & Evidence