Sodium Hydroxide → HCID 22100893, compound
Reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]([C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[C:17]([Cl:22])[CH:16]=1)=[C:9]2[CH2:23][CH2:24][N:25]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:26][CH2:27][CH2:28][CH2:29][C:30]1[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=1)=[O:5])C.[OH-].[Na+]>>[C:39]([O:38][C:36]([N:25]([CH2:26][CH2:27][CH2:28][CH2:29][C:30]1[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=1)[CH2:24][CH2:23][C:9]1[C:8]2[C:12](=[CH:13][CH:14]=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=2)[NH:11][C:10]=1[C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[C:17]([Cl:22])[CH:16]=1)=[O:37])([CH3:42])([CH3:40])[CH3:41]Participants
3
Conditions
- Temperature
- 75 °C
Procedure
To a suspension of 3-{2-[tert-butoxycarbonyl-(4-pyridin-3-yl-butyl)amino]ethyl}-2-(3,5-dichlorophenyl)-1H-indole-5-carboxylic acid ethyl ester (65 mg in 4 mL methanol) at 0° C. was added 1.4 mL of a 1.25N sodium hydroxide solution and the mixture heated to 75° C. on an oil bath. After 2.5 hours the mixture was cooled to room temperature and the reaction quenched by the addition of saturated aqueous ammonium chloride. The mixture was extracted with the ethyl acetate, washed with saturated ammonium chloride solution and the organic portion dried over sodium sulfate. Concentration in vacuo provided the crude title compound (63 mg).
Workup
- temperatureAfter 2.5 hours the mixture was cooled to room temperature
- customthe reaction quenched by the addition of saturated aqueous ammonium chloride
- extractionThe mixture was extracted with the ethyl acetate
- washwashed with saturated ammonium chloride solution
- dry with materialthe organic portion dried over sodium sulfate
- concentrationConcentration in vacuo
Sources & evidence
- ORD record
- ord-43e09e7176c542b5ae189cf46b253e06
- Source dataset
- uspto-grants-1998_12
- Patent number
- US05849764
Reaction notes
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