HCID 18976165, compound → HCID 18976154, compound

Participants

Reaction Conditions

Reaction Steps

12 ml of an aqueous 15% sodium methyl sulfide solution was added to 24 ml of an ethanol solution of 1.635 g of ethyl 3-[3-(3,4-dichlorobenzoylamino)-2,3-dihydro-1-(2-oxiranylmethyl)-2-oxo-1H-indol-3-yl]propionate. The mixture was stirred at 50° C. for 3 hours. The reaction mixture was concentrated, made acidic with aqueous 10% hydrochloric acid and extracted with ethyl acetate. The extract was washed, dried, filtered and then concentrated. The residue was purified by silica gel column chromatography [chloroform-methanol (10:1)] and recrystallized from ethyl acetate-hexane to afford 1.52 g of 3-[3-(3,4-dichlorobenzoylamino)-2,3-dihydro-1-(3-methylthio-2-hydroxypropyl)-2-oxo-1H-indol-3-yl]propionic acid as colorless needles. Melting point: 168.5° to 169.5° C., IR (Nujol) (cm-1): 3400, 3300, 1710, 1650, 1615, FAB-MS (m/z): 499 & 497 (MH+).

Provenance & Evidence