m-Chloroperbenzoic acid → HCID 58577841, compound

HRID 473972Notes

Reaction equation

HRID 473972 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH3:12][C:13]([CH3:45])([CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:34]=[C:33]3[C:28]([C:29]([C:36](=[O:44])[NH:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)=[CH:30][C:31]([CH3:35])=[N:32]3)=[CH:27][CH:26]=2)=[CH:21][N:20]=1)[C:14]([OH:16])=[O:15]>C(Cl)Cl>[C:14]([C:13]([CH3:45])([CH3:12])[CH2:17][O:18][C:19]1[N:20]=[CH:21][C:22]([C:25]2[CH:34]=[C:33]3[C:28]([C:29]([C:36](=[O:44])[NH:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)=[CH:30][C:31]([CH3:35])=[N+:32]3[O-:6])=[CH:27][CH:26]=2)=[CH:23][CH:24]=1)([OH:16])=[O:15]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 46926794HCID 46926794, compound

Product 1

HCID 58577841HCID 58577841, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-Chloroperoxybenzoic acid (30.0 mg, 0.20 mmol) was added at room temperature to a solution of 2,2-dimethyl-3-(5-(2-methyl-4-(phenylcarbamoyl)quinolin-7-yl)pyridin-2-yloxy)propanoic acid B-17 (45.5 mg, 0.10 mmol) in methylene chloride (7 mL). The reaction mixture was stirred at room temperature overnight, then concentrated to dryness under reduced pressure. The residue was purified by flash column chromatography on C18 reverse phase (water:acetonitrile gradient with 0.05% formic acid) to give 7-(6-(2-carboxy-2-methylpropoxy)pyridin-3-yl)-2-methyl-4-(phenylcarbamoyl)quinoline 1-oxide B-23 (16.0 mg, Yield=40%). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.28 (s, 6H), 2.66 (s, 3H), 4.34 (s, 2H), 7.17 (d, J=6.0 Hz, 1H), 7.40-7.46 (m, 3H), 7.80 (d, J=8.0 Hz, 2H), 7.93 (d, J=8.5 Hz, 1H), 7.99 (s, 1H), 8.14 (d, J=8.5 Hz, 1H), 8.41 (d, J=8.5 Hz, 1H), 8.83 (s, 1H), 8.87 (s, 1H), 10.78 (s, 1H). MS (ESI) [M+1]+ 474.

Workup

  1. concentrationconcentrated to dryness under reduced pressure
  2. customThe residue was purified by flash column chromatography on C18 reverse phase (water:acetonitrile gradient with 0.05% formic acid)

Sources & evidence

ORD record
ord-53a3ee21a8d4403fbc49f72b215167ad
Source dataset
uspto-grants-2014_01
Patent number
US08637507B2

Reaction notes

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