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Sodium Hydroxide → 4-(1-Benzyl-3-carbamoylmethyl-2-ethyl-1H-indol-5-yloxy)-butyric acid

HRID 2292796
Notes
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Reaction equation

HRID 2292796 reaction equation
C([O:3][C:4](=[O:31])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]([CH2:25][CH3:26])=[C:12]2[CH2:27][C:28]([NH2:30])=[O:29])C.[OH-].[Na+]>CCO.O>[NH2:30][C:28](=[O:29])[CH2:27][C:12]1[C:11]2[C:15](=[CH:16][CH:17]=[C:9]([O:8][CH2:7][CH2:6][CH2:5][C:4]([OH:31])=[O:3])[CH:10]=2)[N:14]([CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:13]=1[CH2:25][CH3:26]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 105501624-(1-Benzyl-3-carbamoylmethyl-2-ethyl-1H-indol-5-yloxy)-butyric acid ethyl ester

Product 1

HCID 101574724-(1-Benzyl-3-carbamoylmethyl-2-ethyl-1H-indol-5-yloxy)-butyric acidYield 61%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 200 mg (0.5 mmol) of [4-[[3-(2-amino-2-oxoethyl)-2-ethyl-1-(phenylmethyl)-1-H-indol-5-yl]oxy]butanoic acid ethyl ester and 4 mL of 1N NaOH in 10 mL of EtOH was stirred for 1.5 hours, diluted with water and extracted with EtOAc. The aqueous layer was made acidic to pH 5 with 1N HCl, extracted with EtOAc, the EtOAc solution washed with brine and dried (MgSO4). The solvent was evaporated at reduced pressure, the residue stirred with ether/MeOH and the insoluble material filtered to give 120 mg (61% yield) of [4-[[3-(2-amino-2-oxoethyl)-2-ethyl-1-(phenylmethyl)-1-H-indol-5-yl]oxy]butanoic acid, mp, 196°-199° C.

Workup

  1. extractionextracted with EtOAc
  2. extractionextracted with EtOAc
  3. washthe EtOAc solution washed with brine
  4. dry with materialdried (MgSO4)
  5. customThe solvent was evaporated at reduced pressure
  6. stirringthe residue stirred with ether/MeOH
  7. filtrationthe insoluble material filtered

Sources & evidence

ORD record
ord-83ef08c8510f457aa7c8f681f891f0aa
Source dataset
uspto-grants-1997_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05684034

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes