Water → HCID 9966032, compound

Participants

Reaction Steps

Ethyl 4-[(benzyloxycarbonyl)amino]-3-hydroxy-1-methylpyrrole-2-carboxylate Ethyl 4-[(tert-butoxycarbonyl)amino]-3-methoxy-1-methylpyrrole-2-carboxylate (9.0 g, 30.2 mmol) was dissolved in 30 mL ethanol. NaOH (30 ml, 1 M, aq) was added and the solution stirred for 4 days. Water (200 ml) was added and ethanol removed in vacuo. The solution was extracted with diethyl ether, aqueous layer acidified to pH=2-3, and extracted again with diethyl ether. Organic layers were dried over MgSO4, and solvent removed in vacuo to give a white solid (6.0 g, 20.5 mmol, 87% based on recovered SM) 1H NMR (DMSO-d6) δ 12.14 (s, 1H), 8.37 (s, 1H), 6.98 (s, 1H), 3.69 (s, 3H), 3.66 (s, 3H), 1.42 (s, 9H); MS m/e 293.112 (M+H 293.104 calcd. for C12H18N2O5).

Provenance & Evidence