Ethanol → 5-(2-carboxy-ethyl)-3-methyl-1H-pyrrole-2-carboxylic acid ethyl ester

HRID 397431Notes

Reaction equation

HRID 397431 reaction equation
[OH-].[Li+].[CH2:3]([O:5][C:6]([C:8]1[NH:9][C:10]([CH2:14][CH2:15][C:16]([O:18]C(C)(C)C)=[O:17])=[CH:11][C:12]=1[CH3:13])=[O:7])[CH3:4].C(O)C>CO.O>[CH2:3]([O:5][C:6]([C:8]1[NH:9][C:10]([CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:11][C:12]=1[CH3:13])=[O:7])[CH3:4]

Participants

6

Reactant 3

HCID 702EthanolHCID 3939Lithium HydroxideHCID 697094735-(2-tert-butoxycarbonyl-ethyl)-3-methyl-1H-pyrrole-2-carboxylic acid ethyl ester

Product 1

HCID 697080675-(2-carboxy-ethyl)-3-methyl-1H-pyrrole-2-carboxylic acid ethyl esterYield 98.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

Lithium hydroxide (1.02 g, 42.65 mmol) was added to a suspension of 5-(2-tert-butoxycarbonyl-ethyl)-3-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (2.4 g, 8.53 mmol) in methanol (50 mL) and water (12 mL). Ethanol (4 mL) was added to the mixture (to aid solvation of the starting material) and it was stirred at room temperature for overnight. The reaction was diluted with water (20 mL), concentrated (to remove most of the alcohol) and extracted with ether. The aqueous layer was the acidified to pH=2 using 1N HCl (43 mL) and extracted with ethyl acetate (2×). The combined extract was then washed with brine, dried and concentrated to give 1.89 g of 5-(2-carboxy-ethyl)-3-methyl-1H-pyrrole-2-carboxylic acid ethyl ester as a white solid.

Workup

  1. concentrationconcentrated (
  2. customto remove most of the alcohol) and
  3. extractionextracted with ether
  4. extractionextracted with ethyl acetate (2×)
  5. extractionThe combined extract
  6. washwas then washed with brine
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-115692eca5ba47c19b513716b7402b92
Source dataset
uspto-grants-2003_08
Patent number
US06610688B2

Reaction notes

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