Dimethyl Sulfoxide → HCID 131719982, compound

0.55 ml (6.40 mmol) of oxalylchloride was dissolved in 4 ml of anhydrous dichloromethane. To the resultant solution was dropwise added a solution of 0.91 ml (12.8 mmol) of dimethylsulfoxide in 4 ml of anhydrous dichloromethane in a stream of argon gas at -78° C., and the resultant mixture was stirred for 30 minutes. To the mixture was dropwise added a solution of 805 mg (3.26 mmol) of compound 26 obtained in Reference Example 18 in 4 ml of anhydrous dichloromethane, and the resultant mixture was stirred for 2 hours to effect a reaction. To the reaction mixture was added 1.9 ml (25.6 mmol) of triethylamine, and the resultant mixture was stirred for 1 hour to effect a reaction. To the obtained mixture was added a saturated aqueous ammonium chloride solution to thereby terminate the reaction. To the obtained reaction mixture was added chloroform for extraction to obtain an organic layer. The organic layer was separated, washed with saturated saline, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to thereby obtain a residue. The obtained residue was purified by silica gel column chromatography (the composition of the developing solvent was; ethyl acetate:hexane=2:1). As a result, compound 27 (yield: 99%) was obtained as a white crystalline product.

1. customa reaction
2. customa reaction
3. customto thereby terminate
4. customthe reaction
5. customTo the obtained reaction mixture
6. extractionfor extraction
7. customto obtain an organic layer
8. customThe organic layer was separated
9. washwashed with saturated saline
10. dry with materialdried over anhydrous sodium sulfate
11. concentrationconcentrated under reduced pressure
12. customto thereby obtain a residue
13. customThe obtained residue was purified by silica gel column chromatography (the composition of the developing solvent

ORD record

ord-f3bfbd3168c54d8e987793d28b6460c0

Source dataset

uspto-grants-1997_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05621142