Hydrochloric Acid → HCID 19898544, compound

Participants

Reaction Steps

To a rapidly stirred solution of n-propylmagnesium bromide (9 mmol) in anhydrous diethyl ether (20 mL) was added dropwise a solution of 0.641 g (2,25 mmol) of 4-benzyloxycarbonylamino-5-cyclohexyl-2,2-difluoro-3-hydroxy pentanoic acid in anhydrous diethyl ether (10 mL). The mixture was refluxed under nitrogen for two hours after the addition of the acid was completed. The crude mixture was then poured onto a mixture of ice and 0.2N HCl (50 mL). The layers were separated and the aqueous phase was extracted with diethyl ether (3×20 mL). The combined organic layers were washed with a saturated sodium bicarbonate solution and brine. The organic layer was dried over anhydrous magnesium sulphate. Filtration and removal of the solvent in vacuo left an oil. The residue was purified by chromatography (silica gel, ethyl acetate/cyclohexane 1:1) to yield the expected ketone.

Provenance & Evidence