Water → HCID 57221005, compound

HRID 2396323Notes

Reaction equation

HRID 2396323 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].O1CCCC1.O.[OH-].[Li+]>C(OCC)(=O)C>[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 4

HCID 962Water2×HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 67617759HCID 67617759, compound

Product 1

HCID 57221005HCID 57221005, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

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-82886a2192044a24bdfea6d8b79a59ff
Source dataset
uspto-grants-1996_02
Patent number
US05491153

Reaction notes

Loading…