Potassium Hydroxide → HCID 22013005, compound

HRID 1533733Notes

Reaction equation

HRID 1533733 reaction equation
[CH2:1]([O:3][CH:4]([O:41][CH2:42][CH3:43])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH2:26][C:27]([NH:29][C:30]2[CH:35]=[CH:34][C:33]([C:36]([O:38]C)=[O:37])=[CH:32][CH:31]=2)=[O:28])([NH:15][C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)=[O:17])[C:7]1=[O:40])[CH3:2].[OH-].[K+]>CO>[CH2:1]([O:3][CH:4]([O:41][CH2:42][CH3:43])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH2:26][C:27]([NH:29][C:30]2[CH:35]=[CH:34][C:33]([C:36]([OH:38])=[O:37])=[CH:32][CH:31]=2)=[O:28])([NH:15][C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)=[O:17])[C:7]1=[O:40])[CH3:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 22013063HCID 22013063, compound

Product 1

HCID 22013005HCID 22013005, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.588 g of (RS)-1-(2,2-diethoxyethyl)-3-((4-methoxycarbonylphenyl)aminocarbonylmethyl)-3-(N′-(4-methylphenyl)ureido)indolin-2-one in 30 ml of methanol was added 5 ml of an aqueous solution of 0.20 g of potassium hydroxide (85%) at room temperature. The mixture was stirred for 1 day, followed by concentration. The concentrate was diluted with water, and washed with chloroform. The aqueous layer was adjusted to pH 2 with 2N hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate =1/1) to give 0.56 g (98%) of the title compound.

Workup

  1. concentrationfollowed by concentration
  2. additionThe concentrate was diluted with water
  3. washwashed with chloroform
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate =1/1)

Sources & evidence

ORD record
ord-dc4c0074d80f4c4fa7d5dbbb69581aa5
Source dataset
uspto-grants-2001_03
Patent number
US06207836B1

Reaction notes

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