Triethylamine → HCID 58626906, compound

Participants

Reaction Conditions

Reaction Steps

Benzyl 4-isoxazol-3-ylphenylcarbamate (Intermediate 6, 2.26 g, 7.61 mmol) was added to THF and cooled to −78° C. n-Butyl lithium (1.6 M, 5.23 ml, 8.37 mmol) was added. The mixture was allowed to stir for 30 min and then (R)-(−)-glycidyl butyrate (1.19 ml, 8.37 mmol) was added drop wise. The reaction was allowed to stir overnight warning to room temperature, then methanol (5 ml) was added. Saturated NaHCO3 was then added and the product was extracted into EtOAc. The organic layers were washed with brine, then dried over Na2SO4 and concentrated under vacuum to yield crude product. The crude material was dissolved in EtOAc (10 ml) and hexane (10 ml) and the precipitate was collected by filtration. The resulting ((5R)-5-(hydroxymethyl)-3-(4-isoxazol-3-ylphenyl)-1,3-oxazolidin-2-one (780 mg, 2.98 mmol) was added to CH2Cl2 (10 ml) followed by addition of triethylamine (0.496 ml, 3.58 mmol). The solution was cooled to 0° C., and methanesulfonyl chloride (0.253 ml, 3.27 mmol) was added and the reaction was allowed to stir or 2 hours at 0° C. Brine was added and the mixture extracted with CH2Cl2. The organic layers were collected, dried over Na2SO4 and then concentrated under vacuum to yield the product (400 mg).

Provenance & Evidence