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Sodium Hydroxide → HCID 117720296, 화합물

HRID 530249
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HRID 530249 반응식
[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([C@@H:13]3[C@@H:18]([CH3:19])[CH2:17][CH2:16][CH2:15][C:14]3([CH3:21])[CH3:20])=[O:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[OH-].[Na+]>C(O)(=O)C.ClCCl.[Pt](=O)=O>[CH2:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([C@@H:13]3[C@@H:18]([CH3:19])[CH2:17][CH2:16][CH2:15][C:14]3([CH3:20])[CH3:21])=[O:12])=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1
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참가 물질

6

반응물 2

HCID 14798Sodium HydroxideHCID 117720150HCID 117720150, 화합물

생성물 1

HCID 117720296HCID 117720296, 화합물수율 72.3%

시약·촉매·용매 3

HCID 345198Adams' catalyst촉매HCID 176Acetic Acid용매HCID 6344Dichloromethane용매

실험 절차

To a solution of the product of Example 13a (178 mg, 0.63 mmol) in acetic acid (2 mL) was added platinum dioxide (25 mg) and the reaction was stirred at room temperature under an atmosphere of hydrogen for 4 hours. The mixture was diluted with dichloromethane (40 mL) and basified with 1 N NaOH (35 mL) and the organic phase was separated. The aqueous layer was extracted with dichloromethane (30 mL). The combined organic phase was washed with brine (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: dichloromethane/methanol=50/1->10/1) to afford the title compound as a dark brown oil (130 mg, Yield: 72%). 1H NMR (400 MHz, CDCl3) δ 7.76 (d, J=8.4 Hz, 1H), 7.73 (s, 1H), 7.13 (d, J=8.4 Hz, 1H), 4.18 (s, 2H), 3.28 (t, J=6.2 Hz, 2H), 3.01 (t, J=6.2 Hz, 2H), 2.11-2.02 (m, 1H), 1.81-1.77 (m, 1H), 1.61-1.54 (m, 2H), 1.44-1.41 (m, 1H), 1.34-1.24 (m, 3H), 1.10-0.98 (m, 4H), 0.77 (s, 3H), 0.74 (d, J=6.4 Hz, 3H) ppm; Mass spectrum (ESI +ve) m/z 286 (M+H+).

후처리

  1. customthe organic phase was separated
  2. extractionThe aqueous layer was extracted with dichloromethane (30 mL)
  3. washThe combined organic phase was washed with brine (50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: dichloromethane/methanol=50/1->10/1)

출처 및 근거

ORD 기록
ord-6ada8abf14f24b41a75d600a059cca76
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09353063B2

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