Methanol → HCID 57129725, compound

HRID 2082491Notes

Reaction equation

HRID 2082491 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][C:5]([C:6](=[O:24])[CH2:7][CH2:8][NH:9][C:10]2[C:18]3[C:13](=[CH:14][C:15]([Cl:19])=[CH:16][CH:17]=3)[NH:12][C:11]=2[C:20]([O:22]C)=[O:21])=[CH:4][CH:3]=1.[OH-].[Li+].CO.C(OCC)(=O)C>O1CCCC1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6](=[O:24])[CH2:7][CH2:8][NH:9][C:10]2[C:18]3[C:13](=[CH:14][C:15]([Cl:19])=[CH:16][CH:17]=3)[NH:12][C:11]=2[C:20]([OH:22])=[O:21])=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 67619204HCID 67619204, compound

Product 1

HCID 57129725HCID 57129725, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 3-[(p-fluorophenacyl)methylamino]-2-carbmethoxy-6-chloroindole 650 mg, 1.8 mmol) in tetrahydrofuran (10 mL) and water (10 mL). Add lithium hydroxide (227 mg, 5.4 mmol). Add methanol dropwise until an homogeneous solution forms. Stir the reaction at room temperature overnight. Dilute the reaction with water(10 mL) and ethyl acetate (25 mL). Acidify with 1N HCl and separate the layers. Dry the organic phase over magnesium sulfate, filter and concentrate 50% with heat. Reconstitute with hot hexane. Repeat the concentration and reconstitution steps and cool to yield the title compound (560 mg, 90%); mp 2480°-2500C.

Workup

  1. customthe reaction at room temperature overnight
  2. additionDilute
  3. customAcidify with 1N HCl and separate the layers
  4. dry with materialDry the organic phase over magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate 50%
  7. temperaturewith heat
  8. concentrationRepeat the concentration and reconstitution steps
  9. temperaturecool

Sources & evidence

ORD record
ord-c887bffe46fd48f199e8e63ed824c242
Source dataset
uspto-grants-1993_02
Patent number
US05189054

Reaction notes

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