HCID 20616629, compound → HCID 20616635, compound

Participants

Reaction Steps

A suspension of 5(R)-azidomethyl-3-[4-(1-cyanocyclopropan-1-yl)-3-fluorophenyl]oxazolidin-2-one (122 mg) and Lindlar catalyst (12 mg) in methanol (5 mL) was hydrogenated at 1 atm for 3 hours at room temperature. After filtration of the catalyst, the filtrate was concentrated in vacuo to give 5(S)-aminomethyl-3-[4-(1-cyanocyclopropan-1-yl)-3-fluorophenyl]oxazolidin-2-one. To a solution of crude 5(S)-aminomethyl-3-[4-(1-cyanocyclopropan-1-yl)-3-fluorophenyl]oxazolidin-2-one thus obtained in dichloromethane (2 mL) was added pyridine (96 mg) and methanesulfonyl chloride (70 mg) at 0° C., and the mixture was stirred at the same temperature for 30 min. The mixture was washed with water and 5% hydrochloric acid, dried over anhydrous magnesium sulfate, filtered, and then concentrated in vacuo. Flash chromatography (silica, ethyl acetate) of the residue gave N-[5(S)-3-[4-(1-cyanocyclopropan-1-yl)-3-fluorophenyl]-2-oxooxazolidin-5-ylmethyl]methanesulfonylamide. MS (EI+) m/z: 353 (M+).

Provenance & Evidence