Dimethyl Sulfoxide → HCID 68717761, compound

To oxalyl chloride (0.124 mL, 2.0M in dichloromethane) in dichloromethane (2 mL) at −78° C. was added dimethylsulfoxide (0.035 mL) in dichloromethane (0.2 mL). The mixture was stirred for 10 min and the product from Step D (69 mg) was added as a solution in dichloromethane (2 mL). The reaction mixture was stirred for 30 min at −78° C. and triethylamine (17 mL) was added rapidly. After 30 min, the −78° C. bath was removed and the reaction warmed to ambient temperature over 30 min at which point the reaction was quenched with saturated aqueous sodium bicarbonate solution (5 mL) The phases were separated and the aqueous phase extracted with dichloromethane (3×10 mL). The combined organic phases were dried over anhydrous sodium sulfate, filtered, evaporated in vacuo and used without further purification. LC/MS 278.2 (M+1).

1. stirringThe reaction mixture was stirred for 30 min at −78° C.
2. waitAfter 30 min
3. customthe −78° C. bath was removed
4. customwas quenched with saturated aqueous sodium bicarbonate solution (5 mL) The phases
5. customwere separated
6. extractionthe aqueous phase extracted with dichloromethane (3×10 mL)
7. dry with materialThe combined organic phases were dried over anhydrous sodium sulfate
8. filtrationfiltered
9. customevaporated in vacuo
10. customused without further purification

ORD record

ord-1d185dbe309b4eda8c384ef452f55a0c

Source dataset

uspto-grants-2010_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07750034B2