Hydrochloric Acid → HCID 86754774, compound

HRID 1602609Notes

Reaction equation

HRID 1602609 reaction equation
[C:1](=[C:3]1[CH:8]=[C:7]([C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[C:11]([CH3:23])=[C:12]([C:18]([O:20]CC)=[O:19])[NH:13]3)[CH:6]=[CH:5][CH2:4]1)=[O:2].C1COCC1.[Li+].[OH-].Cl>C(OCC)(=O)C.O>[C:1](=[C:3]1[CH:8]=[C:7]([C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[C:11]([CH3:23])=[C:12]([C:18]([OH:20])=[O:19])[NH:13]3)[CH:6]=[CH:5][CH2:4]1)=[O:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 86754775HCID 86754775, compound

Product 1

HCID 86754774HCID 86754774, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 5-carbonylphenyl-3-methyl-indole-2-carboxylate (10 mg, 0.034 mmol) and THF (0.5 mL) was added a solution of LiOH (3.6 mg, 0.15 mmol) and water (0.2 mL). The solution was stirred for 6 h, poured into a mixture of 1 N HCl (1 mL) and ethyl acetate (2 mL). The organic layer was separated, the aqueous layer extracted with ethyl acetate and the combined organic layers was washed with water (1 mL). The solution was dried (MgSO4), filtered and concentrated to give the title compound as a white solid.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer extracted with ethyl acetate
  3. washthe combined organic layers was washed with water (1 mL)
  4. dry with materialThe solution was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-152913ee38114ea190e5eaa092f8ed42
Source dataset
uspto-grants-1999_11
Patent number
US05981762

Reaction notes

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