Sodium Hydroxide → HCID 16065394, 화합물

HRID 2425519노트

반응식

HRID 2425519 반응식
[CH3:1][S:2]([CH2:4][CH2:5][C:6]1[C:7]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[N:8][C:9]2[C:14]([C:15]=1[C:16]([NH:18][C@H:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:20][CH3:21])=[O:17])=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:3].C1C=C(Cl)C=C(C(OO)=[O:42])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+].[OH-].[Na+]>C(Cl)Cl.O>[CH3:1][S:2]([CH2:4][CH2:5][C:6]1[C:7]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[N:8][C:9]2[C:14]([C:15]=1[C:16]([NH:18][C@H:19]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH2:20][CH3:21])=[O:17])=[CH:13][CH:12]=[CH:11][CH:10]=2)(=[O:42])=[O:3]

참가 물질

7

반응물 4

HCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 53325403HCID 53325403, 화합물

생성물 1

HCID 16065394HCID 16065394, 화합물수율 65.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

To a stirring solution of 3-[2-(methylsulfinyl)ethyl]-2-phenyl-N-[(1S)-1-phenylpropyl]quinoline-4-carboxamide (12) (60 mg, 0.13 mmol) in CH2Cl2 at 0° C. was added MCPBA (70-75%, 36 mg, 0.16 mol). The cooling bath was removed and reaction stirred for 2 h, then sodium thiosulfate (1.2 eq.) and H2O (1 mL) were added and suspension stirred until all solids had dissolved. Aqueous 1 N NaOH (1 mL) and CH2Cl2 (2 mL) were then added, the layers shaken together, separated, the organics dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (5-20% EtOAc/CH2Cl2) to give the desired product (40 mg, 65% yield) as a solid. 1H NMR (300 MHz, CDCl3, 52° C.) δ 8.12 (d, J=8.2 Hz, 1H), 7.78-7.65 (m, 2H), 7.56-7.26 (m, 11H), 6.31 (d, J=7.7 Hz, 1H), 5.23 (q, J=7.6 Hz, 1H), 3.36-2.88 (m, 4H), 2.45-2.34 (m, 3H), 2.16-1.88 (m, 2H), 1.04 (t, J=7.4 Hz, 3H); HRMS m/z 473.1878, calcd 473.1899.

후처리

  1. customThe cooling bath was removed
  2. customreaction
  3. stirringsuspension stirred until all solids
  4. dissolutionhad dissolved
  5. stirringthe layers shaken together
  6. customseparated
  7. dry with materialthe organics dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel chromatography (5-20% EtOAc/CH2Cl2)

출처 및 근거

ORD 기록
ord-08e49103f3c64570a06b9bc8e6318972
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07964733B2

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