m-Chloroperbenzoic acid → HCID 18976176, compound

Participants

Reaction Steps

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+).

Provenance & Evidence