Methanol → HCID 57219484, compound

HRID 2082488Notes

Reaction equation

HRID 2082488 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[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][CH:26]=1)[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 67619715HCID 67619715, compound

Product 1

HCID 57219484HCID 57219484, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 3-[(m-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 (550 mg, 89%); mp 258°-260° 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-c6fc2319403543bcb1092aba1fef1fa9
Source dataset
uspto-grants-1993_02
Patent number
US05189054

Reaction notes

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