Sodium Hydroxide → HCID 10499991, compound

HRID 1069588Notes

Reaction equation

HRID 1069588 reaction equation
C([O:3][C:4](=[O:30])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[C:11]([CH2:26][C:27]([NH2:29])=[O:28])=[C:12]([CH3:25])[N:13]2[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)C.[OH-].[Na+]>CCO.O>[NH2:29][C:27](=[O:28])[CH2:26][C:11]1[C:10]2[C:14](=[CH:15][CH:16]=[CH:17][C:9]=2[O:8][CH2:7][CH2:6][CH2:5][C:4]([OH:30])=[O:3])[N:13]([CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:12]=1[CH3:25]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 11795730HCID 11795730, compound

Product 1

HCID 10499991HCID 10499991, compoundYield 42.9%

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-4-yl]oxy]butanoic acid ethyl ester and 2 mL of 1N NaOH in 5 mL of EtOH was stirred for 3.0 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 on concentrating at reduced pressure a precipitate formed that was separated and washed with MeOH to give 40 mg (42% yield) of 4-[[3-(2-amino-2-oxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]butanoic acid, mp, 192-193° C.

Workup

  1. extractionextracted with EtOAc
  2. extractionextracted with EtOAc
  3. dry with materialthe EtOAc dried (MgSO4)
  4. concentrationon concentrating at reduced pressure a precipitate
  5. customformed
  6. customthat was separated
  7. washwashed with MeOH

Sources & evidence

ORD record
ord-71dbd2b7edf4482cb5007897f7a705a3
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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