m-Chloroperbenzoic acid → HCID 18976176, compound

HRID 2393595Notes

Reaction equation

HRID 2393595 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[CH:14]=[C:15]([CH:41]=[CH:42][C:43]=1[Cl:44])[C:16]([NH:18][C:19]1([CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]([CH2:28][CH2:29][CH2:30][S:31][CH3:32])[C:20]1=[O:33])=[O:17]>C(Cl)(Cl)Cl>[Cl:12][C:13]1[CH:14]=[C:15]([CH:41]=[CH:42][C:43]=1[Cl:44])[C:16]([NH:18][C:19]1([CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]([CH2:28][CH2:29][CH2:30][S:31]([CH3:32])=[O:9])[C:20]1=[O:33])=[O:17]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 18976217HCID 18976217, compound

Product 1

HCID 18976176HCID 18976176, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1.22 g of m-chloroperbenzoic acid was added to a stirred solution of 2.05 g of ethyl 3-[3-(3,4-dichlorobenzoylamino)-2,3-dihydro-1-(3-methylthiopropyl)-2-oxo-1H-indol-3-yl]propionate in chloroform (80 ml) under ice cooling. The mixture was stirred at room temperature overnight. After removal of solvent, the residue was extracted with ethyl acetate. The extract was washed with water, dried, and evaporated to dryness under reduced pressure. The residue was separated by silica gel column chromatography [ethyl acetate-hexane (1:2) to chloroform-methanol (20:1)] to afford ethyl 3-[3-(3,4-dichlorobenzoylamino)-2,3-dihydro-1-(3-methylsulfinylpropyl)-2-oxo-1H-indol-3-yl]propionate (a sulfinyl compound, Rf: small) and ethyl 3-[3-(3,4-dichlorobenzoylamino)-2,3-dihydro-1-(3-methylsulfonylpropyl)-2-oxo-1H-indol-3-yl]propionate (a sulfonyl compound, Rf: large). The sulfinyl compound was recrystallized from ethyl acetate-isopropyl ether to afford 1.07 g of the sulfinyl compound as colorless prism. Melting point: 154° to 159° C., IR (Nujol) (cm-1): 3220, 1720, 1655, 1610, FAB-MS (m/z): 527 & 525 (MH+).

Workup

  1. customAfter removal of solvent
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. customevaporated to dryness under reduced pressure
  6. customThe residue was separated by silica gel column chromatography [ethyl acetate-hexane (1:2) to chloroform-methanol (20:1)]

Sources & evidence

ORD record
ord-8f97649e62074cb89e982528e9afa17b
Source dataset
uspto-grants-1998_09
Patent number
US05807883

Reaction notes

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