Sodium Hydroxide → HCID 10594151, compound

HRID 2292788Notes

Reaction equation

HRID 2292788 reaction equation
C[O:2][C:3](=[O:27])[CH2:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[C:8]([CH2:23][C:24]([NH2:26])=[O:25])=[C:9]([CH3:22])[N:10]2[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH-].[Na+]>CCO.O>[NH2:26][C:24](=[O:25])[CH2:23][C:8]1[C:7]2[C:11](=[CH:12][CH:13]=[CH:14][C:6]=2[O:5][CH2:4][C:3]([OH:27])=[O:2])[N:10]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9]=1[CH3:22]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 10761402HCID 10761402, compound

Product 1

HCID 10594151HCID 10594151, compoundYield 62.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 100 mg (0.245 mmol) of 2-[[3-(2-amino-2-oxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]acetic acid methyl ester and 2 mL of 1N NaOH in 5 mL of EtOH was stirred for 2.0 hours, diluted with water and extracted with EtOAc. The aqueous layer was made acidic to pH 6 with 1N HCl and extracted with EtOAc, the EtOAc dried (MgSO4), and concentrated at reduced pressure. The residue was crystallized from MeOH to give 54 mg (57% yield) of 2-[[3-(2-amino-2-oxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]acetic acid, mp, 225°-227° C.

Workup

  1. extractionextracted with EtOAc
  2. extractionextracted with EtOAc
  3. dry with materialthe EtOAc dried (MgSO4)
  4. concentrationconcentrated at reduced pressure
  5. customThe residue was crystallized from MeOH

Sources & evidence

ORD record
ord-fe191db378ff4b18beb629f3b5dfa0d6
Source dataset
uspto-grants-1997_11
Patent number
US05684034

Reaction notes

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