HCID 59556982, compound → HCID 58238347, compound

To a solution of tert-butyl 1-((2S)-2-{[(benzyloxy)carbonyl]amino}-1-(tert-butyldimethylsilyloxy)propyl)cyclopropanecarboxylate (693.9 mg) in methanol (8 mL) was added 10% palladium carbon (containing 50% water, 80 mg), and the mixture was stirred at room temperature for 3 hr under a hydrogen atmosphere and filtered. The filtrate was concentrated under reduced pressure, and the residue was dissolved in methanol (10 mL). Sodium methoxide (404 mg) was added and the mixture was refluxed for 4 hr. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=30/1→1/3) to give the title compound as a colorless solid (yield: 200.8 mg, yield: 60%).

1. filtrationfiltered
2. concentrationThe filtrate was concentrated under reduced pressure
3. dissolutionthe residue was dissolved in methanol (10 mL)
4. additionSodium methoxide (404 mg) was added
5. temperaturethe mixture was refluxed for 4 hr
6. additionA saturated aqueous ammonium chloride solution was added to the reaction mixture
7. extractionthe mixture was extracted with ethyl acetate
8. washThe extract was washed with saturated brine
9. dry with materialdried over anhydrous magnesium sulfate
10. concentrationconcentrated under reduced pressure
11. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=30/1→1/3)

ORD record

ord-c427a53c60b549ccb653f736a34c003f

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08420694B2