Diisopropylethylamine → (5R)-3-[3,5-Difluoro-4-(1,2,3,6-tetrahydropyridin-4-yl)phenyl]-5-[(4-methyl-1,2,3-triazol-1-yl)methyl]oxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

(5R)-3-[4-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)-3,5-difluorophenyl]-5-[(4-methyl-1,2,3-triazol-1-yl)methyl]oxazolidin-2-one (Example 39) (1.74 g, 3.74 mmol) was dissolved in dichloromethane (20 ml) and cooled to 0° C. Diisopropylethylamine (0.13 ml, 0.75 mmol) was added, followed by addition of 1-chloroethylchloroformate (0.48 ml, 4.48 mmol). It was stirred for 30 minutes, then allowed to warm to room temperature. After 16 hours, the reaction mixture was concentrated under vacuum. The intermediate chloroethylcarbamate was dissolved in methanol (20 ml) and heated to reflux. After 30 min, the reaction mixture was cooled to room temperature and concentrated under vacuum to give the title compound as the hydrochloride salt (1.5 g), which was used without further purification.

Provenance & Evidence