Sodium Carbonate → HCID 42605612, 화합물

HRID 470527

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HRID 470527 반응식
C([O-])([O-])=O.[Na+].[Na+].[OH:7][C:8]([CH3:41])([CH3:40])[CH2:9][C@@:10]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:15][C:14](=[O:16])[N:13]([C@H:17]([C:19]2[CH:24]=[CH:23][C:22](B3OC(C)(C)C(C)(C)O3)=[CH:21][CH:20]=2)[CH3:18])[CH2:12][CH2:11]1.Br[C:43]1[CH:44]=[CH:45][C:46](=[O:53])[N:47]([CH2:49][CH:50]2[CH2:52][CH2:51]2)[CH:48]=1>CN(C)C=O>[CH:50]1([CH2:49][N:47]2[C:46](=[O:53])[CH:45]=[CH:44][C:43]([C:22]3[CH:21]=[CH:20][C:19]([C@@H:17]([N:13]4[CH2:12][CH2:11][C@:10]([CH2:9][C:8]([OH:7])([CH3:40])[CH3:41])([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)[O:15][C:14]4=[O:16])[CH3:18])=[CH:24][CH:23]=3)=[CH:48]2)[CH2:52][CH2:51]1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 59532385(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-oneHCID 596357015-Bromo-1-(cyclopropylmethyl)-1,2-dihydropyridin-2-one

생성물 1

HCID 42605612HCID 42605612, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-076bd0fdac2149e780d465a95cb6dc70
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629138B2

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