Water → HCID 57301771, compound

HRID 2082526Notes

Reaction equation

HRID 2082526 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][CH:26]=[CH:25][C:3]=1[C:4](=[O:24])[CH2:5][CH2:6][NH:7][C:8]1[C:16]2[C:11](=[CH:12][C:13]([Cl:18])=[CH:14][C:15]=2[Cl:17])[NH:10][C:9]=1[C:19]([O:21]CC)=[O:20].[OH-].[Li+].O1CCCC1.O>C(OCC)(=O)C>[F:1][C:2]1[CH:28]=[CH:27][CH:26]=[CH:25][C:3]=1[C:4](=[O:24])[CH2:5][CH2:6][NH:7][C:8]1[C:16]2[C:11](=[CH:12][C:13]([Cl:18])=[CH:14][C:15]=2[Cl:17])[NH:10][C:9]=1[C:19]([OH:21])=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 57134806HCID 57134806, compound

Product 1

HCID 57301771HCID 57301771, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Mix 3-[(o-fluorophenacyl)methylamino]-2-carbethoxy-4,6-dichloroindole (600 mg, 1.47 mmol), lithium hydroxide (184 mg, 4.4 mmol), tetrahydrofuran (10 mL) and water (10 mL). Stir for 24 hours at room temperature. Dilute with ethyl acetate (40 mL). Acidify while stirring and separate the layers. Dry the organic phase over magnesium sulfate, filter and concentrate in vacuo. Recrystallize the residue (ethyl acetate/hexane) to yield the title compound as a white powder (480 mg, 86%).

Workup

  1. stirringAcidify while stirring
  2. customseparate the layers
  3. dry with materialDry the organic phase over magnesium sulfate
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customRecrystallize the residue (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-02aa03fd354c49628e1423b8a732abb0
Source dataset
uspto-grants-1993_02
Patent number
US05189054

Reaction notes

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