Sodium Hydroxide → HCID 20469139, compound

HRID 1388935Notes

Reaction equation

HRID 1388935 reaction equation
C([O:3][C:4](=[O:26])[CH2:5][C:6]1[N:7]([CH3:25])[C:8]([C:17]([C:19]2[N:20]([CH3:24])[CH:21]=[CH:22][CH:23]=2)=[O:18])=[C:9]([CH3:16])[C:10]=1[C:11]([O:13]CC)=[O:12])C.[OH-].[Na+]>C(O)C>[CH3:25][N:7]1[C:8]([C:17]([C:19]2[N:20]([CH3:24])[CH:21]=[CH:22][CH:23]=2)=[O:18])=[C:9]([CH3:16])[C:10]([C:11]([OH:13])=[O:12])=[C:6]1[CH2:5][C:4]([OH:26])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20469099HCID 20469099, compound

Product 1

HCID 20469139HCID 20469139, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl-1,4-dimethyl-3-ethoxycarbonyl-5-(1-methylpyrrol-2-oyl)pyrrole-2-acetate (7 g) is dissolved in 20 ml of ethanol, aqueous 50% sodium hydroxide solution (50 ml) is added, and the resulting solution is heated at reflux for about one hour. It is cooled to room temperature, and acidified to yield a white precipitate which in turn is filtered and dried to afford 5.2 g of 1,4-dimethyl-3-hydroxycarbonyl-5-(1-methylpyrrol-2-oyl)pyrrole-2-acetic acid (a diacid). The diacid is partially esterified by treatment with 200 ml of ethanol containing 1.0 g of Bio-Rad® 50W×8 H+ resin at reflux for two hours. After filtration and removal of the excess ethanol, the crude product is purified by HPLC to yield 3.8 g (55%) of white crystalline ethyl 1,4-dimethyl-3-hydroxycarbonyl-5-(1-methylpyrrol-2-oyl)pyrrole-2-acetate.

Workup

  1. temperaturethe resulting solution is heated
  2. temperatureat reflux for about one hour
  3. customto yield a white precipitate which in turn
  4. filtrationis filtered
  5. customdried

Sources & evidence

ORD record
ord-2610d14ee98e47b59e4d61337a8ff0fa
Source dataset
uspto-grants-1984_02
Patent number
US04434175

Reaction notes

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