Methanol → HCID 57123032, compound

HRID 2082493Notes

Reaction equation

HRID 2082493 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[F:27])[C:5](=[O:23])[CH2:6][CH2:7][NH:8][C:9]1[C:17]2[C:12](=[CH:13][C:14]([Cl:18])=[CH:15][CH:16]=2)[NH:11][C:10]=1[C:19]([O:21]C)=[O:20].[OH-].[Li+].CO.C(OCC)(=O)C>O1CCCC1.O>[F:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[F:27])[C:5](=[O:23])[CH2:6][CH2:7][NH:8][C:9]1[C:17]2[C:12](=[CH:13][C:14]([Cl:18])=[CH:15][CH:16]=2)[NH:11][C:10]=1[C:19]([OH:21])=[O:20]

Participants

7

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 67619096HCID 67619096, compound

Product 1

HCID 57123032HCID 57123032, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 3-[(3,4-difluorophenacyl)methylamino]-2-carbmethoxy-6-chloroindole 650 mg, 1.7 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 (510 mg, 82%); mp 260°-264° C.

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-18c3ab22809e460c9b7efcf6b593dc5a
Source dataset
uspto-grants-1993_02
Patent number
US05189054

Reaction notes

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