Water → HCID 178422373, compound

HRID 467584Notes

Reaction equation

HRID 467584 reaction equation
C(OC([N:6]1[C:10]([NH:11][C:12](=[O:23])[C:13]2[CH:18]=[CH:17][C:16]([C:19]([O:21]C)=[O:20])=[CH:15][CH:14]=2)=[C:9]2[CH2:24][N:25]([C:29](=[O:39])[NH:30][C:31]3[C:36]([Cl:37])=[CH:35][CH:34]=[CH:33][C:32]=3[Cl:38])[C:26]([CH3:28])([CH3:27])[C:8]2=[N:7]1)=O)C.[OH-].[Na+].O>CO>[Cl:38][C:32]1[CH:33]=[CH:34][CH:35]=[C:36]([Cl:37])[C:31]=1[NH:30][C:29]([N:25]1[CH2:24][C:9]2[C:8](=[N:7][NH:6][C:10]=2[NH:11][C:12](=[O:23])[C:13]2[CH:14]=[CH:15][C:16]([C:19]([OH:21])=[O:20])=[CH:17][CH:18]=2)[C:26]1([CH3:28])[CH3:27])=[O:39]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 44185220HCID 44185220, compound

Product 1

HCID 178422373HCID 178422373, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 5-(2,6-Dichloro-phenylcarbamoyl)-3-(4-methoxycarbonyl-benzoylamino)-6,6-dimethyl-5,6-dihydro-4H-pyrrolo[3,4-c]pyrazole-2-carboxylic acid ethyl ester (0.4 g, 0.74 mmol) in methanol (5 mL), 2N NaOH aqueous solution (1.00 mL, 2.00 mmol) was added and warmed to 70° C. After 4 hours stirring, water was added (20 mL) and the aqueous solution extracted with ethyl acetate (1×20 mL). The aqueous phase was acidified with 1N HCl solution and extracted with ethyl acetate (2×20 mL). The combined organic phases were dried over sodium sulphate, the solvent evaporated in vacuo yielding 0.33 g (yield 91%) of the title compound as white solid.

Workup

  1. extractionthe aqueous solution extracted with ethyl acetate (1×20 mL)
  2. extractionextracted with ethyl acetate (2×20 mL)
  3. dry with materialThe combined organic phases were dried over sodium sulphate
  4. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-649a3103578d4a9482b5e2f0a90b1323
Source dataset
uspto-grants-2014_01
Patent number
US08623876B2

Reaction notes

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