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

HRID 735329

Reaction equation

HRID 735329 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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+].

Workup

  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

Sources & evidence

ORD record
ord-5c12e8cc79f542cab6f213c9e85cffff
Source dataset
uspto-grants-2009_09
Patent number
US07592456B2

Linked notes

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