Sodium → HCID 9803388, compound

HRID 3345Notes

Reaction equation

HRID 3345 reaction equation
C[O:2][C:3](=[O:34])[CH2:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[C:8]([C:29](=[O:33])[C:30]([NH2:32])=[O:31])=[C:9]([CH3:28])[N:10]2[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Na]>[OH-].[Na+].CO>[NH2:32][C:30](=[O:31])[C:29]([C:8]1[C:7]2[C:11](=[CH:12][CH:13]=[CH:14][C:6]=2[O:5][CH2:4][C:3]([OH:34])=[O:2])[N:10]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:9]=1[CH3:28])=[O:33]

Participants

5

Reactant 2

HCID 5360545SodiumHCID 10813680HCID 10813680, compound

Product 1

HCID 9803388HCID 9803388, compoundYield 36.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 648 mg (1.4 mmol) of [[3-(2-amino-1,2-dioxoethyl)-1-([1,1'-biphenyl]-2-ylmethyl)-2-methyl-1H-indol-4-yl]oxy]acetic acid methyl ester in 10 mL of 1N NaOH and 20 mL of MeOH was heated to maintain reflux for 1 hour, cooled to room temperature and stirred 0.5 hour. The mixture was concentrated, the residue stirred with a mixture of EtOAc/water and the solid material that did not dissolve was filtered and dried to give 227 mg (35% yield) of [[3-(2-amino-1,2-dioxoethyl)-1-([1,1'-biphenyl]-2-ylmethyl)-2-methyl-1H-indol-4-yl]oxy]acetic acid, sodium salt, mp, >265° C.

Workup

  1. temperaturewas heated
  2. temperatureto maintain
  3. temperaturereflux for 1 hour
  4. concentrationThe mixture was concentrated
  5. stirringthe residue stirred with a mixture of EtOAc/water
  6. dissolutionthe solid material that did not dissolve
  7. filtrationwas filtered
  8. customdried

Sources & evidence

ORD record
ord-47a003f9624147efadac55f5c60b94a3
Source dataset
uspto-grants-1998_03
Patent number
US05733923

Reaction notes

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