Acetic Acid → 5-[2-[N-tert-butoxycarbonyl-2-(2-ethoxyphenoxy)ethylamino]propyl]indoline-7-carbonitrile
Reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][C:9]([CH2:15][CH:16]([N:18]([CH2:26][CH2:27][O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[O:35][CH2:36][CH3:37])[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH3:17])=[CH:10][C:11]=2[C:13]#[N:14])[CH2:6][CH2:5]1)(=O)C.[OH-].[Na+].C(O)(=O)C>C(O)C>[C:22]([O:21][C:19]([N:18]([CH2:26][CH2:27][O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[O:35][CH2:36][CH3:37])[CH:16]([CH3:17])[CH2:15][C:9]1[CH:8]=[C:7]2[C:12](=[C:11]([C:13]#[N:14])[CH:10]=1)[NH:4][CH2:5][CH2:6]2)=[O:20])([CH3:25])([CH3:23])[CH3:24]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 1-acetyl-5-[2-[N-tert-butoxycarbonyl-2-(2-ethoxyphenoxy)ethylamino]propyl]indoline-7-carbonitrile (167 mg) in ethanol (2.2 ml) was added a 5N-sodium hydroxide solution (1.1 ml), and the mixture was reacted at room temperature for 2.5 hours. The reaction mixture was neutralized by adding acetic acid, and extracted with methylene chloride. The extract was washed with water and a saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give 133 mg of 5-[2-[N-tert-butoxycarbonyl-2-(2-ethoxyphenoxy)ethylamino]propyl]indoline-7-carbonitrile as an oil.
Workup
- customthe mixture was reacted at room temperature for 2.5 hours
- extractionextracted with methylene chloride
- washThe extract was washed with water
- dry with materiala saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate
- customThe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-0e78d18487e64198836ea2a8fa7e5f46
- Source dataset
- uspto-grants-1995_02
- Patent number
- US05387603
Reaction notes
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