反应详情

温度

-55 °C

Scheme IA, step C: Into a flame dried 500 mL 3 neck flask fitted with a thermometer and magnetic stirrer, DMSO (6.16 mL) in methylene chloride (20 mL) was added dropwise to oxalyl chloride (3.80 mL) in methylene chloride (100 mL) while stirring at −55° C. under a nitrogen atmosphere. After 2 minutes, (2-hydroxycyclopentyl)[(methylethyl)sulfonyl]amine (8.00 g, 38.6 mmol) in methylene chloride (45 mL) was added dropwise at this temperature and the reaction was stirred for an additional 15 minutes. Triethylamine (25.5 mL) was then added dropwise and the reaction was allowed to warm to room temperature. 180 mL of water was added at room temperature and the layers were separated. The organic layer was washed once with water, dried over potassium carbonate, filtered, and concentrated under reduced vacuum to yield 7.83 g as a dark oil. This material was purified via silica gel chromatography employing the Water's Prep. 2000 and eluting with a solvent of methylene chloride/ethyl acetate 9:1 to provide the intermediate title compound (5.76 g, 73%) as a yellow oil. Ion Spray M.S. 204.1 (M*−1). Calculated for C8H15NO3S: Theory: C, 46.81; H, 7.37; N, 6.82. Found: C, 46.56; H, 7.32; N, 6.77.

1. dry with materialScheme IA, step C: Into a flame dried 500 mL 3 neck flask
2. customfitted with a thermometer and magnetic stirrer, DMSO (6.16 mL) in methylene chloride (20 mL)
3. additionwas added dropwise to oxalyl chloride (3.80 mL) in methylene chloride (100 mL)
4. stirringthe reaction was stirred for an additional 15 minutes
5. temperatureto warm to room temperature
6. customthe layers were separated
7. washThe organic layer was washed once with water
8. dry with materialdried over potassium carbonate
9. filtrationfiltered
10. concentrationconcentrated under reduced vacuum
11. customto yield 7.83 g as a dark oil
12. customThis material was purified via silica gel chromatography
13. wash2000 and eluting with a solvent of methylene chloride/ethyl acetate 9:1