m-Chloroperbenzoic acid → Methyl 3-{[7-(4-fluorophenyl)quinolin-3-yl]sulfonyl}propanoate

HRID 735329

반응식

HRID 735329 반응식
ClC1C=C(C=CC=1)C(OO)=O.[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:28]=[C:27]3[C:22]([CH:23]=[C:24]([S:29][CH2:30][CH2:31][C:32]([O:34][CH3:35])=[O:33])[CH:25]=[N:26]3)=[CH:21][CH:20]=2)=[CH:15][CH:14]=1.[OH-:36].[Ca+2].[OH-:38]>ClCCl>[F:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[CH:28]=[C:27]3[C:22]([CH:23]=[C:24]([S:29]([CH2:30][CH2:31][C:32]([O:34][CH3:35])=[O:33])(=[O:38])=[O:36])[CH:25]=[N:26]3)=[CH:21][CH:20]=2)=[CH:17][CH:18]=1

참가 물질

5

반응물 3

HCID 70297m-Chloroperbenzoic acidHCID 6093208Calcium HydroxideHCID 68901143Methyl 3-{[7-(4-fluorophenyl)quinolin-3-yl]thio}propanoate

생성물 1

HCID 68899981Methyl 3-{[7-(4-fluorophenyl)quinolin-3-yl]sulfonyl}propanoate수율 85.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

3-Chloroperoxybenzoic acid (77%; 8.05 g, 36 mmol) was added portionwise to a solution of methyl 3-{[7-(4-fluorophenyl)quinolin-3-yl]thio}propanoate (5.57 g, 16 mmol) in dichloromethane (150 mL). The resulting mixture was stirred at room temperature under nitrogen for 1 hour. Calcium hydroxide (5.1 g, 69 mmol) was added portionwise and the resulting slurry stirred for 30 minutes. The mixture was filtered and the filter cake washed thoroughly with dichloromethane. The filtrate was evaporated and the residue purified by flash chromatography, eluting with 10-15% ethyl acetate/isohexane, to give methyl 3-{[7-(4-fluorophenyl)quinolin-3-yl]sulfonyl}propanoate as a white solid (5.09 g, 84%). 1H NMR (500 MHz, CDCl3) δ 9.30 (1H, d, J 2.2 Hz), 8.77 (1H, d, J 2.0 Hz), 8.39 (1H, s), 8.06 (1H, d, J 8.5 Hz), 7.95 (1H, dd, J 1.7, 8.5 Hz), 7.77-7.73 (2H, m), 7.25-7.21 (2H, m), 3.61 (3H, s), 3.59 (2H, t, J 7.5 Hz), 2.86 (2H, t, J 7.5 Hz); m/z (ES+) 374 [MH+].

후처리

  1. stirringthe resulting slurry stirred for 30 minutes
  2. filtrationThe mixture was filtered
  3. washthe filter cake washed thoroughly with dichloromethane
  4. customThe filtrate was evaporated
  5. customthe residue purified by flash chromatography
  6. washeluting with 10-15% ethyl acetate/isohexane

출처 및 근거

ORD 기록
ord-5c12e8cc79f542cab6f213c9e85cffff
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592456B2

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