Sodium Hydroxide → HCID 16065394、化合物

HRID 2425519ノート

反応式

HRID 2425519 の反応式
[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]

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 53325403HCID 53325403、化合物

生成物 1

HCID 16065394HCID 16065394、化合物収率 65.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-08e49103f3c64570a06b9bc8e6318972
出典データセット
uspto-grants-2011_06
特許番号
US07964733B2

反応ノート

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