Methanol → HCID 118157400, compound

Temperature

-78 °C

Under a nitrogen atmosphere, ethyl 8-hexylsulfamoyl-octanoate (No. 6804262; 818.3 mg, 2.44 mmol) was dissolved in toluene (11 mL), and the mixture was cooled to −78° C. While maintaining the temperature at −78° C., a diluted solution of diisobutylaluminum hydride (1.5 M solution in toluene, 1.95 mL, 2.93 mmol) in toluene (2.9 mL) was added dropwise over 25 minutes, and the mixture was stirred at −78° C. for 1.5 hours. The reaction was monitored by LCMS. To this reaction solution was, then, further added a diluted solution of diisobutylaluminum hydride (1.5 M solution in toluene, 0.81 mL, 1.22 mmol) in toluene (0.9 mL) was added dropwise over 10 minutes, and the mixture was stirred at −78° C. for 1 hour. Methanol (0.65 mL) was added to the reaction solution, which was stirred at −78° C. for 10 minutes to stop the reaction. A saturated aqueous solution (3.0 mL) of Rochelle salt and water (9.0 mL) were further added and the mixture was stirred at 0° C. for 1 hour. Insoluble material was filtered off and washed with dichloromethane. The filtrate was then extracted with dichloromethane. The organic layer was washed with water, and dried over anhydrous sodium sulfate, and then filtered. Dichloromethane was distilled off to obtain the target 8-oxo-octane-1-sulfonic acid hexyl amide (ESI (LC/MS positive mode) m/z 292 (M+H); Rt 1.68 min.).

1. temperatureWhile maintaining the temperature at −78° C.
2. additionwas added dropwise over 10 minutes
3. stirringthe mixture was stirred at −78° C. for 1 hour
4. stirringwas stirred at −78° C. for 10 minutes
5. customthe reaction
6. stirringthe mixture was stirred at 0° C. for 1 hour
7. filtrationInsoluble material was filtered off
8. washwashed with dichloromethane
9. extractionThe filtrate was then extracted with dichloromethane
10. washThe organic layer was washed with water
11. dry with materialdried over anhydrous sodium sulfate
12. filtrationfiltered
13. distillationDichloromethane was distilled off

ORD record

ord-a4331c44a8614cf4be493043829db1ce

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09266853B2