Methyl iodide → HCID 10380418, compound

Temperature

0 °C

To a solution of 4-chloro-N-[(1S,2S)-1-(hydroxymethyl)-2-methylbutyl]benzenesulfonamide (0.10 g, 0.343 mmol) dissolved in DMF (2.0 mL) was added potassium carbonate (47 mg, 0.343 mmol). After 30 minutes, the reaction mixture was cooled to 0° C. and iodomethane (50 μL, 0.686 mmol) was added. After 2 hours, the ice bath was removed and the reaction mixture was stirred at 25° C. for 24 hours. The insolubles were then filtered off and the DMF solution was diluted with EtOAc (50 mL) and washed sequentially with 10% citric acid (50 mL) and saturated brine (50 mL), dried over MgSO4 and evaporated to a clear oil which was washed with Et2O and then purified by flash chromatography (eluant: 95-5 CHCl3/iPrOH) to afford the desired product as a clear oil (71 mg, 68%). Mass Spectrum (+APCI): 306 ([M+H]+). Anal: Calc'd for C13H20ClNO3S: C, 51.06; H, 6.59; N, 4.58. Found: C, 51.15; H, 6.73; N, 4.36.

1. waitAfter 2 hours
2. customthe ice bath was removed
3. filtrationThe insolubles were then filtered off
4. additionthe DMF solution was diluted with EtOAc (50 mL)
5. washwashed sequentially with 10% citric acid (50 mL) and saturated brine (50 mL)
6. dry with materialdried over MgSO4
7. customevaporated to a clear oil which
8. washwas washed with Et2O
9. custompurified by flash chromatography (eluant: 95-5 CHCl3/iPrOH)

ORD record

ord-bbbf1346823c4eda8f125446391222b3

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07671075B2