Hydrochloric Acid → HCID 131736820, compound

Participants

Reaction Steps

4-Nitrobenzoyl chloride (105 g) was added in small portions to a solution of benzyl (5R)-5-(2-(benzyloxy)-2-oxoethyl)-3-(3-hydroxyphenyl)-4,5-dihydro-1,2-oxazole-5-carboxylate (126 g) in pyridine (380 mL) at 20 C. The obtained mixture was stirred at room temperature for 1.5 hours. To the reaction mixture, ethyl acetate (650 mL) and 1 M hydrochloric acid (1300 mL) were added at 0 C, and then, ethyl acetate (1300 mL) and water (260 mL) were added. The organic layer was separated, and the aqueous layer was subjected to extraction with ethyl acetate (1300 mL). Combined organic layers were washed with diluted aqueous ammonia ((28% aqueous ammonia (26 mL)/water (1300 mL))×2), 1 M hydrochloric acid (1300 mL×2), and brine (1300 mL) and dried over anhydrous sodium sulfate, and then, the solvent was distilled off under reduced pressure. The residue was washed with diisopropyl ether (1500 mL) to obtain the title compound (165 g).

Provenance & Evidence