Lithium Hydroxide → HCID 57221005, compound

HRID 2082485Notes

Reaction equation

HRID 2082485 reaction equation
[CH2:1]([CH2:10][NH:11][C:12]1[C:20]2[C:15](=[CH:16][C:17]([Cl:21])=[CH:18][CH:19]=2)[NH:14][C:13]=1[C:22]([O:24]C)=[O:23])[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3].[OH-].[Li+].C(OCC)(=O)C>O1CCCC1.O>[CH2:1]([CH2:10][NH:11][C:12]1[C:20]2[C:15](=[CH:16][C:17]([Cl:21])=[CH:18][CH:19]=2)[NH:14][C:13]=1[C:22]([OH:24])=[O:23])[C:2]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)=[O:3]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 67617759HCID 67617759, compound

Product 1

HCID 57221005HCID 57221005, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 3-[(phenacyl)methylamino]-2-carbmethoxy-6-chloroindole from above, in tetrahydrofuran (5 mL) and water (5 mL). Add lithium hydroxide and stir for 8 hours at 40° C. Dilute the reaction with water(10 mL) and ethyl acetate (10 mL). Separate the layers and acidify the aqueous layer. Extract the aqueous with ethyl acetate, dry the organic phase over magnesium sulfate, filter and concentrate in vacuo. Recrystallize from ethyl acetate/hexane to yield the title compound (75 mg); mp 250°-255° C.

Workup

  1. additionDilute
  2. customSeparate the layers
  3. extractionExtract the aqueous with ethyl acetate
  4. dry with materialdry the organic phase over magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customRecrystallize from ethyl acetate/hexane

Sources & evidence

ORD record
ord-e65af37afea04e60a4b00e16d0463c28
Source dataset
uspto-grants-1993_02
Patent number
US05189054

Reaction notes

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