Methanol → 4-[5-(1-Imidazolylmethyl)-thien-2-yl]-4-oxobutyric acid

HRID 2164395Notes

Reaction equation

HRID 2164395 reaction equation
C[O:2][C:3](=[O:19])[CH2:4][CH2:5][C:6]([C:8]1[S:9][C:10]([CH2:13][C:14]2[NH:15][CH:16]=[CH:17][N:18]=2)=[CH:11][CH:12]=1)=[O:7].[OH-].[Na+].CO>O>[NH:18]1[CH:17]=[CH:16][N:15]=[C:14]1[CH2:13][C:10]1[S:9][C:8]([C:6](=[O:7])[CH2:5][CH2:4][C:3]([OH:19])=[O:2])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 704876864-[5-(1-Imidazolylmethyl)-thien-2-yl]-4-oxo-butyric acid methyl ester

Product 1

HCID 704292984-[5-(1-Imidazolylmethyl)-thien-2-yl]-4-oxobutyric acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4.17 g of 4-[5-(1-imidazolylmethyl)-thien-2-yl]-4-oxo-butyric acid methyl ester, 0.8 g of sodium hydroxide and 20 ml of methanol is stirred at room temperature for 8 hours. The solvent is then stripped off and the residue is taken up in water. The solution is extracted several times with chloroform, and the chloroform phase is discarded. The aqueous solution is brought to about pH 7 with dilute hydrochloric acid and is concentrated to dryness. The residue is purified by column chromatography (silica gel/CHCl3 /methanol).

Workup

  1. extractionThe solution is extracted several times with chloroform
  2. concentrationis concentrated to dryness
  3. customThe residue is purified by column chromatography (silica gel/CHCl3 /methanol)

Sources & evidence

ORD record
ord-ec16d96664ce4c5a8672c2a1e115f8be
Source dataset
uspto-grants-1985_03
Patent number
US04504479

Reaction notes

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