m-Chloroperbenzoic acid → HCID 21186241, compound

HRID 361441Notes

Reaction equation

HRID 361441 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH2:12]([O:16][C:17]([N:19]([C:39]1[C:44]([O:45][CH3:46])=[N:43][C:42]([CH3:47])=[CH:41][N:40]=1)[S:20]([C:23]1[C:24]([C:29]2[CH:34]=[CH:33][C:32]([CH2:35][C:36]([CH3:38])=[CH2:37])=[CH:31][CH:30]=2)=[N:25][CH:26]=[CH:27][CH:28]=1)(=[O:22])=[O:21])=[O:18])[CH:13]([CH3:15])[CH3:14]>>[O:6]1[CH2:37][C:36]1([CH3:38])[CH2:35][C:32]1[CH:33]=[CH:34][C:29]([C:24]2[C:23]([S:20]([N:19]([C:17]([O:16][CH2:12][CH:13]([CH3:14])[CH3:15])=[O:18])[C:39]3[C:44]([O:45][CH3:46])=[N:43][C:42]([CH3:47])=[CH:41][N:40]=3)(=[O:22])=[O:21])=[CH:28][CH:27]=[CH:26][N:25]=2)=[CH:30][CH:31]=1

Participants

3

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 21186230HCID 21186230, compound

Product 1

HCID 21186241HCID 21186241, compoundYield 8.6%

Procedure

3-Chloroperoxybenzoic acid (50%, 2.4 g) was added over 5 minutes to a solution of N-(isobutoxycarbonyl)-N-(3-methoxy-5-methylpyrazin-2-yl)-2-[4-(2-methylprop-2-enyl)phenyl]pyridine-3-sulphonamide (1.8 g) in dichloromethanc (75 ml) at 0° C. The reaction mixture was allowed to warm to ambient temperature and stirred a further 1 hour. The mixture was washed with saturated aqueous sodium hydrogen carbonate solution (20 ml), water and saturated sodium chloride solution then dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by suction flash chromatography followed by gradient elution with 0-40% ethyl acetate/hexane through a silica gel Mega Bond Elut column to give 2-[4-(2,3-epoxy-2-methylpropyl)phenyl]-N-(isobutoxycarbonyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (0.16 g) as a solid, 1H NMR (CDCl3): 0.65 (d, 6 H), 1.3 (s, 3 H), 1.7 (m, 1 H), 2.5 (s, 3 H), 2.65 (dd, 2 H), 2.9 (q, 2 H), 3.85 (d, 2 H), 4.0 (s, 3 H), 7.3 (d, 2 H), 7.5 (dd, 1 H), 7.6 (d, 2 H), 7.95 (s, 1 H), 8.85 (dd, 1 H), 8.95 (dd, 1 H); mass spectrum (+ve ESP): 527 (M+H)+.

Workup

  1. washThe mixture was washed with saturated aqueous sodium hydrogen carbonate solution (20 ml), water and saturated sodium chloride solution
  2. dry with materialthen dried (MgSO4)
  3. customVolatile material was removed by evaporation
  4. customthe residue was purified by suction flash chromatography
  5. washfollowed by gradient elution with 0-40% ethyl acetate/hexane through a silica gel Mega Bond Elut column

Sources & evidence

ORD record
ord-ad3e75984655428c92bac8f83ccaacee
Source dataset
uspto-grants-1999_02
Patent number
US05866568

Reaction notes

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