Hydrochloric Acid → HCID 178457438, compound

Participants

Reaction Steps

To a solution of 5-benzyloxy-6-hydroxy-2-(8-phenyl-1,4-dioxa-spiro[4.5]dec-8-ylmethyl)-pyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-isopropylamide (271) (500 mg, 0.74 mmol) in tetrahydrofuran (30.0 mL) was added 2.1N aqueous HCl (6.0 mL) and stirred at room temperature for 7 h while silica thin layer chromatography was performed (only ethyl acetate; Rf=0.25). The reaction mixture was concentrated in vacuum and diluted with ethyl acetate (50 mL), washed with aqueous NaHCO3 solution (20 mL) and brine (30 mL) and dried and concentrated in vacuum to get a crude mass which was purified by CombiFlash using a gradient eluent mixture of methanol and dichloromethane to get pure 5-benzyloxy-6-hydroxy-2-(4-oxo-1-phenyl-cyclohexylmethyl)-pyrimidine-4-carboxylic acid (2-hydroxyethyl)-isopropylamide (272) (255 mg, 66.6%) as a white sticky solid.

Provenance & Evidence