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Water → HCID 178471530, 화합물

HRID 1713869
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HRID 1713869 반응식
C(=O)([O-])[O-].[Cs+].[Cs+].[C:7](=[NH:20])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.FC(F)(F)S(O[C:27]1[CH:32]=[CH:31][C:30]([C@H:33]2[CH2:38][CH2:37][C@H:36]([CH:39]([CH3:45])[C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH2:35][CH2:34]2)=[CH:29][CH:28]=1)(=O)=O.O>C1COCC1.CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:8]1([C:7](=[N:20][C:27]2[CH:32]=[CH:31][C:30]([C@H:33]3[CH2:34][CH2:35][C@H:36]([CH:39]([CH3:45])[C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH2:37][CH2:38]3)=[CH:29][CH:28]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 136809Benzophenone imineHCID 178471539HCID 178471539, 화합물

생성물 1

HCID 178471530HCID 178471530, 화합물수율 59%

시약·촉매·용매 3

HCID 167845palladium(II) acetate
촉매
HCID 8028Tetrahydrofuran용매
HCID 8857Ethyl Acetate용매

실험 절차

Caesium carbonate (4.0 g, 12.4 mmol), R-BINAP (330 mg, 0.53 mmol), palladium acetate (119 mg, 0.53 mmol) and benzophenone imine (2.2 mL, 13.2 mmol) were added sequentially, each in one portion, to a stirred solution of trans-ethyl 2-[4-(4-{[(trifluoromethyl)-sulfonyl]oxy}phenyl)cyclohexyl]propanoate in THF (50 mL) and the reaction mixture was heated at 65° C. for 70 h under an argon atmosphere. The reaction mixture was cooled to room temperature and concentrated in vacuo to leave a residue. The residue was taken up in EtOAc (75 mL) and H2O (25 mL) was added. The layers were separated and the organic layer was extracted with brine (25 mL), dried and concentrated in vacuo to leave a residue. The residue was purified by chromatography, eluting with 10-50% EtOAc in isohexane, to give the title compound (2.3 g, 59%) as an oil; 1H NMR δ (CDCl3) 1.07-1.25 (2H, m), 1.15 (3H, d), 1.3 (3H, t), 1.35-1.5 (2H, m), 1.55-1.7 (2H, m), 1.72-1.8 (1H, m), 1.83-1.95 (2H, m), 2.24-2.43 (2H, m), 4.15 (2H, q), 6.7 (2H, d), 7.0 (2H, d), 7.15 (2H, d), 7.23-7.35 (1H, m), 7.4 (2H, dd), 7.47-7.55 (2H, m), 7.78 (2H, d), 7.84 (1H, d); MS m/e MH+ 440.

후처리

  1. concentrationconcentrated in vacuo
  2. customto leave a residue
  3. customThe layers were separated
  4. extractionthe organic layer was extracted with brine (25 mL)
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customto leave a residue
  8. customThe residue was purified by chromatography
  9. washeluting with 10-50% EtOAc in isohexane

출처 및 근거

ORD 기록
ord-b70b59adf28842538ab709797f445e11
출처 데이터셋
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07795283B2

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