HCID 18976165, compound → HCID 18976154, compound

HRID 2393601Notes

Reaction equation

[CH3:1][S:2][CH3:3].[Na].[Cl:5][C:6]1[CH:7]=[C:8]([CH:33]=[CH:34][C:35]=1[Cl:36])[C:9]([NH:11][C:12]1([CH2:26][CH2:27][C:28]([O:30]CC)=[O:29])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([CH2:21][CH:22]2C[O:23]2)[C:13]1=[O:25])=[O:10]>C(O)C>[Cl:5][C:6]1[CH:7]=[C:8]([CH:33]=[CH:34][C:35]=1[Cl:36])[C:9]([NH:11][C:12]1([CH2:26][CH2:27][C:28]([OH:30])=[O:29])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([CH2:21][CH:22]([OH:23])[CH2:1][S:2][CH3:3])[C:13]1=[O:25])=[O:10]

Participants

Conditions

Temperature: 50 °C

Procedure

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+).

Workup

concentrationThe reaction mixture was concentrated
extractionextracted with ethyl acetate
washThe extract was washed
customdried
filtrationfiltered
concentrationconcentrated
customThe residue was purified by silica gel column chromatography [chloroform-methanol (10:1)]
customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record: ord-afedaeca9278411ba2d4f92cf77d2b0c
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05807883

Reaction notes

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