Sodium Hydroxide → HCID 19024844, compound

HRID 1034086Notes

Reaction equation

[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([NH:22][C:23]2[CH:24]=[C:25]([CH:44]=[CH:45][CH:46]=2)[C:26]([C:28]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[N:30]([CH2:37][CH2:38][C:39]([O:41]CC)=[O:40])[CH:29]=2)=[O:27])[C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH:19]([CH3:21])[CH3:20])=[CH:14][CH:13]=2)=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[OH-].[Na+]>O1CCOCC1.CO>[CH2:18]([C:15]1[CH:16]=[CH:17][C:12]([CH:11]([NH:22][C:23]2[CH:24]=[C:25]([CH:44]=[CH:45][CH:46]=2)[C:26]([C:28]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[N:30]([CH2:37][CH2:38][C:39]([OH:41])=[O:40])[CH:29]=2)=[O:27])[C:8]2[CH:7]=[CH:6][C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])=[CH:10][CH:9]=2)=[CH:13][CH:14]=1)[CH:19]([CH3:20])[CH3:21]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of ethyl 3-[3-[3-[bis(4-isobutylphenyl)methylamino]benzoyl]indol-1-yl]propionate (507 mg) in a mixture of 1,4-dioxane (8 ml) and methanol (2 ml) was added 1N aqueous sodium hydroxide (2 ml), and the mixture was stirred at 25° C. for 5 hours. After evaporation of the organic solvent, the residue was acidified (pH 2) with 1N hydrochloric acid, and extracted with ethyl acetate. The extract was washed with water and dried over magnesium sulfate. After evaporation of the solvent, the residue was chromatographed on silica gel (20 g) eluting with chloroform to give 3-[3-[3-[bis(4-isobutylphenyl)methylamino]benzoyl]indol-1-yl]propionic acid (375 mg) as an oil.

Workup

customAfter evaporation of the organic solvent
extractionextracted with ethyl acetate
washThe extract was washed with water
dry with materialdried over magnesium sulfate
customAfter evaporation of the solvent
customthe residue was chromatographed on silica gel (20 g)
washeluting with chloroform

Sources & evidence

ORD record: ord-88340d37dd10443bae0fa480c5e590cd
Source dataset: uspto-grants-1994_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05312829

Reaction notes

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