反应详情

温度

5 °C

To a chilled (5° C.) and stirred slurry of the alcohol title product of Example 4 (154.0 g, 0.54 mol) and triethylamine (81.76 ml, 59.6 g, 0.589 mol) in methylene chloride (3.0 liters), a solution of methanesulfonyl chloride (43.55 ml, 64.5 g, 0.563 mol) in methylene chloride (350 ml) was added dropwise over 30 minutes. TLC monitoring (methylene chloride/methanol=9:1 in volume; iodoplatinate spray) of the reaction mixture after an additional 1/2 hour of stirring indicated incomplete reaction. Complete reaction was realized within 1/2 hour after addition of a second portion of triethylamine (8.23 ml, 6.0 g, 59.3 mmol) and methanesulfonyl chloride [4.32 ml, 6.4 g, 55.9 mmol) added dropwise as a methylene chloride (20 ml) solution]. Water (3 liters) and methylene chloride (1.5 liters) were added, and the biphasic mixture was vigorously stirred prior to separation of the organic and aqueous phases. The aqueous portion was then extracted with a fresh portion of methylene chloride (1.5 liters). The organic extracts were then combined, washed with brine (twice with 2 liter portions) and dried over anhydrous sodium sulfate. Concentration in vacuo afforded the present title compound as a tan solid (178.0 g, 90.2% yield). TLC Rf (methylene chloride/methanol=9:1 in volume; iodoplatinate spray): 0.24. MS m/z 365.1 (M, C17H23N3O4S). 13CNMR (CDCl3) delta 164.0, 160.9, 129.6, 122.4, 122.1, 116.0, 110.5, 71.9, 59.9, 57.7, 54.0, 53.3, 48.1, 37.4, 35.9, 28.4, 26.2.

1. customreaction
2. customComplete reaction
3. customto separation of the organic and aqueous phases
4. extractionThe aqueous portion was then extracted with a fresh portion of methylene chloride (1.5 liters)
5. washwashed with brine (twice with 2 liter portions) and
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationConcentration in vacuo