Potassium Hydroxide → HCID 22013003, compound

HRID 1533718Notes

Reaction equation

HRID 1533718 reaction equation
[OH-].[K+].C([O:5][C:6]([CH2:8][C:9]1([NH:19][C:20]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=2)=[O:21])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][C:10]1=[O:18])=[O:7])C>O.C(O)C>[OH:7][C:6]([CH2:8][C:9]1([NH:19][C:20]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=2)=[O:21])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][C:10]1=[O:18])=[O:5]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 22013034HCID 22013034, compound

Product 1

HCID 22013003HCID 22013003, compoundYield 27.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 300 mg of potassium hydroxide (85%) in 2 ml of water was added to a solution of 0.35 g of (RS)-3-(ethoxycarbonylmethyl)-3-(N′-(4-methylphenyl)ureido)indolin-2-one in 10 ml of ethanol at room temperature, and the mixture was stirred for 4 hours, followed by concentration. The concentrate was diluted with water, and washed with chloroform. The aqueous layer was adjusted to pH 3 by addition of 2N hydrochloric acid, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated. The resulting crude product was recrystallized from isopropyl alcohol to give 0.088 g (27%) of the title compound.

Workup

  1. concentrationfollowed by concentration
  2. additionThe concentrate was diluted with water
  3. washwashed with chloroform
  4. additionThe aqueous layer was adjusted to pH 3 by addition of 2N hydrochloric acid
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated
  8. customThe resulting crude product was recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-366eeb8d4e0e4a858c867af5feb7e045
Source dataset
uspto-grants-2001_03
Patent number
US06207836B1

Reaction notes

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