Dimethylamine → HCID 57541258, compound

Temperature

0 °C

Dimethylamine in THF (57.9 ml, 116 mmol) was dissolved in dichloromethane (29.0 ml) and cooled to 0° C. Then, methyl (chlorosulfonyl)acetate (prepared according to: Szymonifka, M. J.; Heck, J. V. Tet. Lett. 1989, 30, 2869-72.) (10.0 g, 57.9 mmol) was added dropwise as a solution in dichloromethane (29.0 ml), while maintaining the temperature below 5° C. The resulting solution was allowed to warm to room temperature over the course of 2 h. Then, brine (200 mL) was added and the aqueous phase was extracted with dichloromethane (3×100 mL). The combined organics were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (EtOAc/Hexanes gradient) to afford the title compound as a yellow liquid. 1H NMR (600 MHz, DMSO-D6) δ 4.25 (s, 2H); 3.68 (s, 3H); 2.78 (s, 6H). LRMS (APCI) calculated for C5H12NO4S [M+H]+, 182.0; found 182.0.

1. temperaturewhile maintaining the temperature below 5° C
2. temperatureto warm to room temperature over the course of 2 h
3. extractionthe aqueous phase was extracted with dichloromethane (3×100 mL)
4. dry with materialThe combined organics were dried over anhydrous Na2SO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by column chromatography on silica gel (EtOAc/Hexanes gradient)

ORD record

ord-26444211b7324c0798823f4f3acecc69

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08101603B2