Sodium Hydroxide → 2-[[3-(2-amino-1,2-dioxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]propanoic acid

HRID 581118Notes

Reaction equation

HRID 581118 reaction equation
C[O:2][C:3](=[O:29])[CH:4]([O:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[C:9]([C:24](=[O:28])[C:25]([NH2:27])=[O:26])=[C:10]([CH3:23])[N:11]2[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:5].[OH-].[Na+]>CO>[NH2:27][C:25](=[O:26])[C:24]([C:9]1[C:8]2[C:12](=[CH:13][CH:14]=[CH:15][C:7]=2[O:6][CH:4]([CH3:5])[C:3]([OH:29])=[O:2])[N:11]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10]=1[CH3:23])=[O:28]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 105967932-[[3-(2-amino-1,2-dioxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]propanoic acid methyl ester

Product 1

HCID 98000062-[[3-(2-amino-1,2-dioxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]propanoic acidYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 521 mg (1.3 mmol) of dl-2-[[3-(2-amino-1,2-dioxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]propanoic acid methyl ester and 10 mL of 1N NaOH in 30 mL of methanol was heated to maintain reflux for 0.17 hours, cooled to room temperature and stirred for 0.5 hour. The mixture was concentrated at reduced pressure and the residue taken up in EtOAc/water. The aqueous layer was separated, made acidic to pH 2-3 with 1N HCl and extracted with EtOAc. The EtOAc solution was concentrated at reduced pressure and the residue stirred with a EtOAc-ether mixture. The insoluble material was filtered to give 246 mg (50% yield) of dl-2-[[3-(2-amino-1,2-dioxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]propanoic acid, mp, 201-204° C.

Workup

  1. temperaturewas heated
  2. temperatureto maintain
  3. temperaturereflux for 0.17 hours
  4. concentrationThe mixture was concentrated at reduced pressure
  5. customThe aqueous layer was separated
  6. extractionextracted with EtOAc
  7. concentrationThe EtOAc solution was concentrated at reduced pressure
  8. stirringthe residue stirred with a EtOAc-ether mixture
  9. filtrationThe insoluble material was filtered

Sources & evidence

ORD record
ord-5ffb43df1bbc4954b7737fb28282e0e9
Source dataset
uspto-grants-1999_07
Patent number
US05919810

Reaction notes

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