Ethanol → HCID 59454101, compound

A mixture of tert-butyl [(1S,2R)-2-(hydrazinocarbonyl)cyclopentyl]carbamate (370 mg) and ethanol (5.6 ml) was ice-cooled, and dithioxomethane (230 μl) and potassium hydroxide (120 mg) were added thereto in this order, followed by stirring at the same temperature for 30 minutes. The reaction mixture was stirred at room temperature for 1 hour, warmed, and heated for 6 hours under reflux. The reaction mixture was left to be cooled, and water (50 ml) and diethyl ether (50 ml) were added thereto, followed by liquid separation. The aqueous layer was ice-cooled, and 1 M hydrochloric acid was added thereto to adjust the pH to about 4, followed by extraction with ethyl acetate (50 ml). The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was washed with diisopropyl ether (5 ml) to obtain tert-butyl [(1S,2R)-2-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)cyclopentyl]carbamate (308 mg) as a white solid.

1. temperaturecooled
2. stirringThe reaction mixture was stirred at room temperature for 1 hour
3. temperaturewarmed
4. temperatureheated for 6 hours
5. temperatureunder reflux
6. waitThe reaction mixture was left
7. temperatureto be cooled
8. customfollowed by liquid separation
9. temperaturecooled
10. addition1 M hydrochloric acid was added
11. extractionfollowed by extraction with ethyl acetate (50 ml)
12. washThe organic layer was washed with saturated brine
13. dry with materialdried over anhydrous magnesium sulfate
14. concentrationconcentrated under reduced pressure
15. washThe residue was washed with diisopropyl ether (5 ml)

ORD record

ord-5a0a6b0bf49c403b864eddd595da8607

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08030489B2