Dimethyl Sulfoxide → HCID 57652408, compound

Temperature

0 °C

Oxalyl chloride (141 μL) was dissolved in methylene chloride (1 mL). To the solution, a solution of dimethyl sulfoxide (176 μL) in methylene chloride (1 mL) was added dropwise at −78° C., and the mixture was stirred for 15 minutes. A solution of the compound (168 mg) obtained in Step 5 in methylene chloride (2 mL) was added dropwise thereto at −78° C., and the mixture was stirred for 2 hours. Triethylamine (695 μL) was added thereto, and the mixture was heated to 0° C. and then stirred overnight. To the reaction solution, methylene chloride was added, and the organic layer was washed with water and saturated sodium chloride solution, then dried over anhydrous sodium sulfate, and filtered. The solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluting solvent: hexane/ethyl acetate=9/1-7/3) to obtain the title compound (113 mg).

1. stirringat −78° C., and the mixture was stirred for 2 hours
2. stirringstirred overnight
3. washthe organic layer was washed with water and saturated sodium chloride solution
4. dry with materialdried over anhydrous sodium sulfate
5. filtrationfiltered
6. distillationThe solvent was distilled off under reduced pressure
7. customThe obtained residue was purified by silica gel column chromatography (eluting solvent: hexane/ethyl acetate=9/1-7/3)

ORD record

ord-2d118024e8c64df9b72df3e5dcd3c1e2

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08609710B2