1-Chloroethyl chloroformate → HCID 57697514, compound

Temperature

90 °C

To a solution of the compound (0.30 g) obtained in Example 8 in acetonitrile (10 mL) was added 1-chloroethyl chloroformate (0.13 mL) at room temperature, and the mixture was stirred at 90° C. for 2 hr. The reaction mixture was concentrated under reduced pressure, and then the obtained residue was dissolved in MeOH (10 mL), and the mixture was stirred at 80° C. for 1 hr. The reaction mixture was concentrated under reduced pressure, and the obtained residue was dissolved in ethyl acetate and water, and made basic with aqueous sodium hydroxide solution. The resultant product was extracted with ethyl acetate, and concentrated. The residue was purified by silica gel column chromatography (solvent gradient; 50% ethyl acetate/hexane→0.1% aqueous ammonia/ethyl acetate) to give the title compound (0.085 g, 42%) as a white powder.

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. dissolutionthe obtained residue was dissolved in MeOH (10 mL)
3. stirringthe mixture was stirred at 80° C. for 1 hr
4. concentrationThe reaction mixture was concentrated under reduced pressure
5. dissolutionthe obtained residue was dissolved in ethyl acetate
6. extractionThe resultant product was extracted with ethyl acetate
7. concentrationconcentrated
8. customThe residue was purified by silica gel column chromatography (solvent gradient; 50% ethyl acetate/hexane→0.1% aqueous ammonia/ethyl acetate)

ORD record

ord-8503c64bf9fb4a6293334f0b1ce68fc3

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08158617B2