反应详情

Methanesulfonyl chloride (0.841 mL, 1.25 g, 10.87 mmol) is added to di-tert-butyl (1S,2R,3S,4R,5R,6R)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]-4-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylate (2.00 g, 3.40 mmol), triethylamine (1.66 mL, 1.20 g, 11.89 mmol), and tetrahydrofuran (33.98 mL, 30.11 g, 417.61 mmol) at 0° C. and stirred. Gradually warm the reaction to room temperature and stir overnight. Dilute the reaction with saturated aqueous sodium bicarbonate then extract with ethyl acetate (3×100 mL). The combined organic extracts are washed with brine, dried over magnesium sulfate, filtered, and then concentrated under reduced pressure to yield a residue. The residue is purified by flash chromatography using eluting with 5-60% ethyl acetate in hexanes to give the title compound (1.40 g, 2.10 mmol, 62%).

1. temperatureGradually warm
2. customthe reaction to room temperature
3. stirringstir overnight
4. additionDilute
5. extractionthen extract with ethyl acetate (3×100 mL)
6. washThe combined organic extracts are washed with brine
7. dry with materialdried over magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customto yield a residue
11. customThe residue is purified by flash chromatography
12. washusing eluting with 5-60% ethyl acetate in hexanes