Hydrochloric Acid → HCID 54689879, compound

Participants

Reaction Steps

To a solution of 1.91 g (3.65 mmol) of 4-(4-benzyloxy-3,5-dichloro-phenyl)-2-(2-methoxycarbonyl-acetylamino)-thiophene-3-carboxylic acid ethyl ester in 20 mL of THF was added 600 mg (15 mmol) of 60% NaH in mineral oil. The reaction was stirred at reflux under N2 for 18 h, then the excess NaH was quenched by the addition of 10 mL of water. The THF was removed in vacuo, then the remaining solution was taken up in 30 mL of 2M NaOH(aq.) and 30 mL of ethanol. This was stirred at 80° C. for 5 h, then concentrated to remove most of the ethanol. The remaining solution was diluted with 100 mL of water, and extracted with diethyl ether (2×30 mL). The ether layers were discarded, along with a small amount of precipitate that formed in the aqueous layer. The stirred aqueous layer was made acidic with 4M HCl to give a precipitate. Diethyl ether was added and the mixture was stirred to suspend the precipitate in the ether layer, then most of the water was decanted. The precipitate was filtered, and washed with water, then diethyl ether to give 1.20 g (79%) of the titled compound as a tan solid. MS (ESI) m/e 417.7, (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 5.05 (s, 1H) 5.76 (s, 1H) 7.23 (s, 1H) 7.43 (m, 2H) 7.58 (m, 2H) 11.15 (s, 1H).

Provenance & Evidence