Water → HCID 86753114, compound

HRID 2393613Notes

Reaction equation

HRID 2393613 reaction equation
C(=O)([O-])[O-].[K+:5].[K+].O.[F:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([O:24][CH3:25])[CH:22]=2)[C:17]([CH2:39][CH2:40][C:41]([OH:43])=[O:42])([NH:26][C:27]([C:29]2[N:30]=[CH:31][C:32]3[C:37]([CH:38]=2)=[CH:36][CH:35]=[CH:34][CH:33]=3)=[O:28])[C:16]1=[O:44]>C(#N)C>[F:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([O:24][CH3:25])[CH:22]=2)[C:17]([CH2:39][CH2:40][C:41]([O-:43])=[O:42])([NH:26][C:27]([C:29]2[N:30]=[CH:31][C:32]3[C:37]([CH:38]=2)=[CH:36][CH:35]=[CH:34][CH:33]=3)=[O:28])[C:16]1=[O:44].[K+:5]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 18976143HCID 18976143, compound

Product 1

HCID 86753114HCID 86753114, compoundYield 161.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.74 g of potassium carbonate, 5 ml of water and 20 ml of acetonitrile were added to 11.47 g of (+)-3-[1-(2-fluorophenyl)-2,3-dihydro-3-(3-isoquinolinyl)carbonylamino-6-methoxy-2-oxo-1H-indol-3-yl]propionic acid. After removal of solvent under reduced pressure, the residue was dissolved in 100 ml of acetonitrile was added to the residue under heating, and insolubles were filtered off. The filtrate was concentrated, and the residue was dissolved in 100 ml of acetonitrile under heating. After cooling, precipitated crystals were collected by filtration to afford 10.91 g of (+)-potassium 3-[1-(2-fluorophenyl)-2,3-dihydro-3-(3-isoquinolinyl)carbonylamino-6-methoxy-2-oxo-1H-indol-3-yl]-propionate as a colorless solid. Melting point 275° to 277° C. (decomposed). FAB-MS (m/z): 576 (MK+), 538 (MH+), 192, 39 (base). [α]D25 : +91.8° (c=0.438, methanol).

Workup

  1. customAfter removal of solvent under reduced pressure
  2. dissolutionthe residue was dissolved in 100 ml of acetonitrile
  3. additionwas added to the residue
  4. temperatureunder heating
  5. filtrationinsolubles were filtered off
  6. concentrationThe filtrate was concentrated
  7. dissolutionthe residue was dissolved in 100 ml of acetonitrile
  8. temperatureunder heating
  9. temperatureAfter cooling
  10. customprecipitated crystals
  11. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-7bbb4dfa208943edb3eb6c72b5f8b33f
Source dataset
uspto-grants-1998_09
Patent number
US05807883

Reaction notes

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