Potassium Hydroxide → HCID 15458211, compound

HRID 1953328Notes

Reaction equation

HRID 1953328 reaction equation
C([O:3][C:4]([CH2:6][C:7]1([NH:25][C:26]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=2)=[O:27])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([CH2:16][CH:17]([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20])[C:8]1=[O:24])=[O:5])C.[OH-].[K+]>CO>[CH2:22]([O:21][CH:17]([O:18][CH2:19][CH3:20])[CH2:16][N:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7]([CH2:6][C:4]([OH:5])=[O:3])([NH:25][C:26]([NH:28][C:29]2[CH:30]=[CH:31][C:32]([CH3:35])=[CH:33][CH:34]=2)=[O:27])[C:8]1=[O:24])[CH3:23]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 22013036HCID 22013036, compound

Product 1

HCID 15458211HCID 15458211, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 8.21 g of (RS)-3-(ethoxycarbonylmethyl)-1-(2,2-diethoxyethyl)-3-(N'-(4-methylphenyl)ureido)indolin-2-one in 100 ml of methanol was added 30 ml of an aqueous solution of 2.0 g of potassium hydroxide (85%) at room temperature, followed by stirring for 6 hours. The reaction mixture was concentrated, and the concentrate was diluted with water, which was washed with chloroform. The aqueous layer was adjusted to pH 2 by addition of 2N hydrochloric acid, and extracted with chloroform, and the organic layer was dried over anhydrous sodium sulfate and concentrated to yield 6.63 g (86%) of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe concentrate was diluted with water, which
  3. washwas washed with chloroform
  4. additionThe aqueous layer was adjusted to pH 2 by addition of 2N hydrochloric acid
  5. extractionextracted with chloroform
  6. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5a63edbd0aef43379741db8e28e0e172
Source dataset
uspto-grants-2000_09
Patent number
US06114536

Reaction notes

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