Sodium Hydroxide → 4-(1-Benzyl-3-carbamoylmethyl-2-methyl-1H-indol-6-yloxy)-butyric acid

HRID 2292782Notes

Reaction equation

HRID 2292782 reaction equation
C([O:3][C:4](=[O:30])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:17]=[C:16]2[C:12]([C:13]([CH2:26][C:27]([NH2:29])=[O:28])=[C:14]([CH3:25])[N:15]2[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:11][CH:10]=1)C.[OH-].[Na+]>CCO.O>[NH2:29][C:27](=[O:28])[CH2:26][C:13]1[C:12]2[C:16](=[CH:17][C:9]([O:8][CH2:7][CH2:6][CH2:5][C:4]([OH:30])=[O:3])=[CH:10][CH:11]=2)[N:15]([CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:14]=1[CH3:25]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 105735094-(1-Benzyl-3-carbamoylmethyl-2-methyl-1H-indol-6-yloxy)-butyric acid ethyl ester

Product 1

HCID 107860284-(1-Benzyl-3-carbamoylmethyl-2-methyl-1H-indol-6-yloxy)-butyric acidYield 47.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 100 mg (0.245 mmol) of 4-[[3-(2-amino-2-oxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-6-yl]oxy]butanoic acid ethyl ester and 2 mL of 1N NaOH in 5 mL of EtOH was stirred for 1.5 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/CH2Cl2 to give 44 mg (47% yield) of 4-[[3-(2-amino-2-oxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-6-yl]oxy]butanoic acid, mp, 180°-184° 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/CH2Cl2

Sources & evidence

ORD record
ord-08efa6b2ffc1497193acd33118f7ac8d
Source dataset
uspto-grants-1997_11
Patent number
US05684034

Reaction notes

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