4-Toluenesulfonyl chloride → tert-butyl N-{2-[(4-methylbenzenesulfonyl)oxy]ethyl}carbamate

Temperature

0 °C

A solution of p-toluenesulfonyl chloride (28.40 g, 148 mmol) in dichloromethane (100 mL) was added dropwise over 30 minutes at 0° C. to a mixture of tert-butyl N-(2-hydroxyethyl)carbamate (20 g, 120 mmol), triethylamine (18.80 g, 186 mmol) and trimethylammonium chloride (1.18 g, 12.4 mmol) in dichloromethane (120 mL). The mixture was stirred at 0° C. for 1 hour then filtered, washing with dichloromethane (100 mL). The filtrate was washed with 10% citric acid (3×100 mL) and brine (100 mL). The organic layer was dried with magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure to give an oil. The oil was dissolved in ethyl acetate (40 mL) and then iso-hexane (160 mL) was added slowly. The resultant slurry was stirred at room temperature for 17 hours and then filtered. The collected solid was washed with iso-hexane (240 mL) to yield the title compound as a colourless powder (25 g, 64%).

1. filtrationthen filtered
2. washwashing with dichloromethane (100 mL)
3. washThe filtrate was washed with 10% citric acid (3×100 mL) and brine (100 mL)
4. dry with materialThe organic layer was dried with magnesium sulfate
5. filtrationfiltered
6. concentrationThe filtrate was concentrated under reduced pressure
7. customto give an oil
8. stirringThe resultant slurry was stirred at room temperature for 17 hours
9. filtrationfiltered
10. washThe collected solid was washed with iso-hexane (240 mL)

ORD record

ord-ba88e398b2c94a9b83c0f7eaf1a5c4b1

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07169921B2