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

HRID 735329

Reaktionsgleichung

Reaktionsgleichung von HRID 735329
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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 68899981Methyl 3-{[7-(4-fluorophenyl)quinolin-3-yl]sulfonyl}propanoateAusbeute 85,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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+].

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-5c12e8cc79f542cab6f213c9e85cffff
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592456B2

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