Water → HCID 22175631, compound

HRID 1797658Notes

Reaction equation

HRID 1797658 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:43])[NH:17][CH2:18][C:19]3[N:20]([CH2:39][CH:40]([CH3:42])[CH3:41])[C:21](=[O:38])[C:22]4[C:27]([C:28]=3[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:26][C:25]([C:35]([NH2:37])=[S:36])=[CH:24][CH:23]=4)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Br[CH2:45][C:46](=O)[CH3:47].O>C(O)C>[CH2:39]([N:20]1[C:19]([CH2:18][NH:17][C:16](=[O:43])[O:15][CH2:14][CH:12]2[C:13]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[C:6]3[C:11]2=[CH:10][CH:9]=[CH:8][CH:7]=3)=[C:28]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([C:35]3[S:36][CH:45]=[C:46]([CH3:47])[N:37]=3)[CH:26]=2)[C:21]1=[O:38])[CH:40]([CH3:41])[CH3:42]

Participants

5

Reactant 3

HCID 962WaterHCID 11715BromoacetoneHCID 22175953HCID 22175953, compound

Product 1

HCID 22175631HCID 22175631, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 9H-fluoren-9-ylmethyl[6-(aminocarbothioyl)-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.47 g, 0.8 mmol) and bromoacetone (0.22 g, 1.6 mmol) in ethanol (10 ml) was refluxed under heating for 1 h. The reaction mixture was poured into water and extracted with ethyl. acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 9H-fluoren-9-ylmethyl [2-isobutyl-6-(4-methyl-1,3-thiazol-2-yl)-1-oxo-4phenyl-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.41 g, 82.0%) as an amorphous.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 1 h
  3. extractionextracted with ethyl
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-34a8fc2e841a4821b6fbd9cb7b0696fd
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

Loading…