Methanol → HCID 178524865, compound

Participants

Reaction Steps

A mixture of 5-benzyloxy-6-hydroxy-2-(8-phenyl-1,4-dioxa-spiro[4.5]dec-8-ylmethyl)-pyrimidine-4-carboxylic acid tert-butyl ester (269) (850 mg, 1.60 mmol), LiOH.H2O (670 mg, 15.96 mmol) in tetrahydrofuran-water (5:1, 48 mL) was refluxed for 20 h while silica thin layer chromatography was performed (methanol:dichloromethane=1:9, Rf=0.1). Tetrahydrofuran was removed from the reaction mixture in vacuo and the residue was diluted with water (25 mL), cooled in ice water, neutralized to about pH 7 with 1N aqueous HCl and extracted with ethyl acetate (2×50 mL). The combined organic parts were washed with brine (25 mL), dried and concentrated in vacuo to get pure 5-benzyloxy-6-hydroxy-2-(8-phenyl-1,4-dioxa-spiro[4.5]dec-8-ylmethyl)-pyrimidine-4-carboxylic acid (270) (700 mg, 92.05%) as a yellow solid.

Provenance & Evidence