Water → HCID 69402396, compound

HRID 1797660Notes

Reaction equation

HRID 1797660 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)[C:47]([O:49][CH2:50][CH3:51])=[O:48].O>C(O)C>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:17][CH2:18][C:19]3[N:20]([CH2:39][CH:40]([CH3:41])[CH3:42])[C:21](=[O:38])[C:22]4[C:27]([C:28]=3[C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)=[CH:26][C:25]([C:35]3[S:36][CH:45]=[C:46]([C:47]([O:49][CH2:50][CH3:51])=[O:48])[N:37]=3)=[CH:24][CH:23]=4)=[O:43])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 66144Ethyl bromopyruvateHCID 22175953HCID 22175953, compound

Product 1

HCID 69402396HCID 69402396, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 9H-fluoren-9-ylmethyl[6-(aminocarbothioyl)-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl]methylcarbamate (Example 194(2)) (2.35 g, 4 mmol) and ethyl bromopyruvate (1.56 g, 8 mmol) in ethanol (20 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 ethyl 2-[3-[[[(9H-fluoren-9-ylmethoxy)carbony]amino]methyl]-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-6-isoquinolinyl]-1,3-thiazole-4-carboxylate (1.92 g, 70.3%) as crystals.

Workup

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

Sources & evidence

ORD record
ord-224347c573eb4c4e923ae6bb2c6c90fe
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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