Water → (4-{[(2-Cyano-ethyl)-(4-dipropylamino-butyl)-amino]-methyl}-benzyl)-carbamic acid t-butyl ester

HRID 2080799Notes

Reaction equation

HRID 2080799 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH:16][CH2:17][CH2:18][CH2:19][CH2:20][N:21]([CH2:25][CH2:26][CH3:27])[CH2:22][CH2:23][CH3:24])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].O.[C:30](#[N:33])[CH:31]=[CH2:32]>CO>[C:1]([O:5][C:6](=[O:28])[NH:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][N:16]([CH2:32][CH2:31][C:30]#[N:33])[CH2:17][CH2:18][CH2:19][CH2:20][N:21]([CH2:22][CH2:23][CH3:24])[CH2:25][CH2:26][CH3:27])=[CH:13][CH:14]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 7855AcrylonitrileHCID 66941782{4-[(4-dipropylamino-butylamino)-methyl]-benzyl}-carbamic Acid t-butyl Ester

Product 1

HCID 67103530(4-{[(2-Cyano-ethyl)-(4-dipropylamino-butyl)-amino]-methyl}-benzyl)-carbamic acid t-butyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (260 mg) obtained in Example 23-4 was dissolved in methanol (5.0 ml) and added with distilled water (1.0 ml) and acrylonitrile (87.4 μl) and the whole was stirred overnight at room temperature. After completion of the reaction, the solvent was distilled off and the resultant was subjected to extraction with chloroform and washed with a saturated saline solution. The organic layer was dried with anhydrous sodium sulfate. The solvent was distilled off, thereby obtaining the subject compound (332 mg) as a colorless oily substance.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. extractionthe resultant was subjected to extraction with chloroform
  4. washwashed with a saturated saline solution
  5. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  6. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-a345aefe554e4f76a6ff0c104c11fb55
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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