Rac-{[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1h-indol-3-yl]-isopropyl-amino}-acetic acid ethyl ester → HCID 57479232, compound

HRID 556488Notes

Reaction equation

HRID 556488 reaction equation
C([O:3][C:4](=[O:29])[CH2:5][N:6]([C:10]1([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=2)[C:18]2[C:13](=[CH:14][C:15]([Cl:19])=[CH:16][CH:17]=2)[NH:12][C:11]1=[O:20])[CH:7]([CH3:9])[CH3:8])C>CO.[OH-].[K+]>[Cl:19][C:15]1[CH:14]=[C:13]2[C:18]([C:10]([N:6]([CH2:5][C:4]([OH:29])=[O:3])[CH:7]([CH3:9])[CH3:8])([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=3)[C:11](=[O:20])[NH:12]2)=[CH:17][CH:16]=1

Participants

4

Reactant 1

HCID 57479121Rac-{[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1h-indol-3-yl]-isopropyl-amino}-acetic acid ethyl ester

Product 1

HCID 57479232HCID 57479232, compoundYield 75.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

rac-{[6-Chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-isopropyl-amino}-acetic acid ethyl ester (4.5 g, 10.4 mmol) was dissolved in a mixture of MeOH and KOH aqueous solution. This mixed solution was refluxed overnight and then the solution was concentrated. The PH of water layer was adjusted to 5-6 and then the water layer was extracted with dichloromethane. The organic layer was dried, concentrated and purified by chromatography to obtain 3.2 g solid rac-{[6-Chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-isopropyl-amino}-acetic acid.

Workup

  1. temperatureThis mixed solution was refluxed overnight
  2. concentrationthe solution was concentrated
  3. extractionthe water layer was extracted with dichloromethane
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. custompurified by chromatography

Sources & evidence

ORD record
ord-fe88c89212f544e7a9e2a5c08f29fba9
Source dataset
uspto-grants-2011_11
Patent number
US08058269B2

Reaction notes

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