反应详情

温度

0 °C

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).

1. additionwas added
2. stirringto stir overnight
3. customwarning to room temperature
4. extractionthe product was extracted into EtOAc
5. washThe organic layers were washed with brine
6. dry with materialdried over Na2SO4
7. concentrationconcentrated under vacuum
8. customto yield crude product
9. filtrationhexane (10 ml) and the precipitate was collected by filtration
10. stirringto stir or 2 hours at 0° C
11. extractionthe mixture extracted with CH2Cl2
12. customThe organic layers were collected
13. dry with materialdried over Na2SO4
14. concentrationconcentrated under vacuum