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Acetic Acid → 5-[2-[N-tert-butoxycarbonyl-2-(2-ethoxyphenoxy)ethylamino]propyl]indoline-7-carbonitrile

HRID 273855
Notes
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Reaction equation

HRID 273855 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 200943581-acetyl-5-[2-[N-tert-butoxycarbonyl-2-(2-ethoxyphenoxy) ethylamino]propyl]indoline-7-carbonitrile

Product 1

HCID 200943835-[2-[N-tert-butoxycarbonyl-2-(2-ethoxyphenoxy)ethylamino]propyl]indoline-7-carbonitrileYield 86.8%

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

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

  1. customthe mixture was reacted at room temperature for 2.5 hours
  2. extractionextracted with methylene chloride
  3. washThe extract was washed with water
  4. dry with materiala saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0e78d18487e64198836ea2a8fa7e5f46
Source dataset
uspto-grants-1995_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05387603

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes