Dimethyl Sulfoxide → HCID 59556910, compound

A solution of oxalyl chloride (0.050 mL) in methylene chloride (2.0 mL) was cooled to −60° C., dimethyl sulfoxide (0.062 mL) was added dropwise, and the mixture was stirred at the same temperature for 30 min. A solution of 2-chloro-4-[(6S,7R)-7-hydroxy-6-methyl-4-oxo-5-azaspiro[2.4]hept-5-yl]benzonitrile (40.1 mg) in methylene chloride (2.5 mL) was added dropwise to the reaction mixture, and the mixture was stirred at −40° C. for 1 hr. Triethylamine (0.202 mL) was added, and the mixture was stirred at 0° C. for 30 min. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=50/1→1/1) to give the title compound as a pale-yellow oil (yield: 35 mg, 88%).

1. stirringthe mixture was stirred at −40° C. for 1 hr
2. stirringthe mixture was stirred at 0° C. for 30 min
3. extractionthe mixture was extracted with ethyl acetate
4. dry with materialThe extract was dried over anhydrous magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=50/1→1/1)

ORD record

ord-924efa90cf9d44feb9f8385d550161b5

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08420694B2