Sodium Carbonate → 3-{(S)-1-[4-(1-Cyclopropylmethyl-6-oxo-1,6-dihydro-pyridin-3-yl)-phenyl]-ethyl}-(S)-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-[1,3]oxazinan-2-one

온도

100 °C

2 M aqueous Na2CO3 solution (0.84 mL) was added to a solution of (S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-[(S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl]-1,3-oxazinan-2-one (0.40 g) and 5-bromo-1-cyclopropylmethyl-1H-pyridin-2-one (0.24 g) in dimethyl-formamide (4 mL). The resulting mixture was sparged with argon for 10 min, before [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) dichloromethane complex (34 mg) was added. The mixture was heated to 100° C. and stirred at this temperature for 4 h. After cooling to ambient temperature, water was added and the resulting mixture was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4), and concentrated. The residue was purified by chromatography on silica gel (dichloromethane/methanol 99:1->95:5) to afford the title compound that was crystallized with little ethyl acetate. Yield: 0.19 g (46% of theory); Mass spectrum (ESI+): m/z=501 [M+H]+.

1. customThe resulting mixture was sparged with argon for 10 min, before [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) dichloromethane complex (34 mg)
2. additionwas added
3. temperatureAfter cooling to ambient temperature
4. additionwater was added
5. extractionthe resulting mixture was extracted with ethyl acetate
6. washThe combined organic extracts were washed with brine
7. dry with materialdried (MgSO4)
8. concentrationconcentrated
9. customThe residue was purified by chromatography on silica gel (dichloromethane/methanol 99:1->95:5)

ORD 기록

ord-076bd0fdac2149e780d465a95cb6dc70

출처 데이터셋

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08629138B2