2-[(1-Acetyl-2-indolyl)carbonylamino]-4-(2,4-dimethoxyphenyl)-5-ethoxycarbonylmethylthiazole → 2-[(2-Indolyl)carbonylamino]-4-(2,4-dimethoxyphenyl)-5-carboxymethylthiazol

HRID 1034189Notes

Reaction equation

HRID 1034189 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[C:5]1[C:13]([NH:15][C:16]1[S:17][C:18]([CH2:31][C:32]([O:34]CC)=[O:33])=[C:19]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=2[O:29][CH3:30])[N:20]=1)=[O:14])(=O)C>C(O)C>[NH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[C:5]1[C:13]([NH:15][C:16]1[S:17][C:18]([CH2:31][C:32]([OH:34])=[O:33])=[C:19]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=2[O:29][CH3:30])[N:20]=1)=[O:14]

Participants

3

Reactant 1

HCID 189465652-[(1-Acetyl-2-indolyl)carbonylamino]-4-(2,4-dimethoxyphenyl)-5-ethoxycarbonylmethylthiazole

Product 1

HCID 189465792-[(2-Indolyl)carbonylamino]-4-(2,4-dimethoxyphenyl)-5-carboxymethylthiazol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.5 g of 2-[(1-acetyl-2-indolyl)carbonylamino]-4-(2,4-dimethoxyphenyl)-5-ethoxycarbonylmethylthiazole, prepared above according to Example 10, is dissolved in 10 ml of 950 ethanol and then 1.5 ml of 2N NAOH are added. The reaction mixture is stirred overnight at room temperature and then concentrated under vacuum. The residue is taken up in a buffer solution, pH=2, a precipitate is separated by filtration, washed with water, filtered and then rinsed with ether.

Workup

  1. addition1.5 ml of 2N NAOH are added
  2. concentrationconcentrated under vacuum
  3. customa precipitate is separated by filtration
  4. washwashed with water
  5. filtrationfiltered
  6. washrinsed with ether

Sources & evidence

ORD record
ord-9dc1469100b142ad8d3fb2f72dc569fa
Source dataset
uspto-grants-1994_05
Patent number
US05314889

Reaction notes

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