Ethanol → HCID 18976196, compound

HRID 2393604Notes

Reaction equation

HRID 2393604 reaction equation
[OH-].[Na+].O.[Cl:4][C:5]1[CH:6]=[C:7]([CH:37]=[CH:38][C:39]=1[Cl:40])[C:8]([NH:10][C:11]1([CH2:30][CH2:31][C:32]([O:34]CC)=[O:33])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([CH2:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:12]1=[O:29])=[O:9].C(O)C>O1CCCC1>[Cl:4][C:5]1[CH:6]=[C:7]([CH:37]=[CH:38][C:39]=1[Cl:40])[C:8]([NH:10][C:11]1([CH2:30][CH2:31][C:32]([OH:34])=[O:33])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([CH2:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:12]1=[O:29])=[O:9]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 18976214HCID 18976214, compound

Product 1

HCID 18976196HCID 18976196, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.5 ml of 4N sodium hydroxide and 5 ml of water were added to a mixed solution of 1.20 g of ethyl 3-[3-(3,4-dichlorobenzoylamino)-2,3-dihydro-2-oxo-1-(3-phenylpropyl)-1H-indol-3-yl]propionate, 20 ml of ethanol and 5 ml of tetrahydrofuran. The mixture was stirred at room temperature for 7 hours. The reaction mixture was concentrated under reduced pressure, diluted with water, then made acidic with 10% hydrochloric acid and extracted with ethyl acetate. After the extract was dried, the solvent was removed by evaporation. The residue was recrystallized from ethanol-ethyl acetate to afford 1.09 g of 3-[3-(3,4-dichlorobenzoylamino)-2,3-dihydro-2-oxo-1-(3-phenylpropyl)-1H-indol-3-yl]propionic acid as colorless needles. Melting point: 242° to 243° C., IR (Nujol) (cm-1): 3285, 1715, 1690, 1675, 1615, FAB-MS (m/z): 513 & 511 (MH+).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate
  4. customAfter the extract was dried
  5. customthe solvent was removed by evaporation
  6. customThe residue was recrystallized from ethanol-ethyl acetate

Sources & evidence

ORD record
ord-63a569a3254d4b468585aeea289e1972
Source dataset
uspto-grants-1998_09
Patent number
US05807883

Reaction notes

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