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

HRID 735329

反応式

HRID 735329 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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+].

後処理

  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

出典と根拠

ORDレコード
ord-5c12e8cc79f542cab6f213c9e85cffff
出典データセット
uspto-grants-2009_09
特許番号
US07592456B2

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