Water → HCID 21829916, compound

HRID 1600539Notes

Reaction equation

HRID 1600539 reaction equation
O=[C:2]([CH3:20])[CH2:3][N:4]([C:12](=[O:19])[CH2:13][C:14]1[CH:18]=[CH:17][S:16][CH:15]=1)[C:5]([CH3:11])([CH3:10])[C:6]([O:8]C)=[O:7].C[O-].[Na+].O.[OH-].[K+]>C(O)C>[CH3:20][C:2]1[CH2:3][N:4]([C:5]([CH3:11])([CH3:10])[C:6]([OH:8])=[O:7])[C:12](=[O:19])[C:13]=1[C:14]1[CH:18]=[CH:17][S:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 10942334Sodium MethoxideHCID 67574269HCID 67574269, compound

Product 1

HCID 21829916HCID 21829916, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl 2-[N-(2-oxopropyl)thiophene-3-yl-acetylamino]isobutyrate (7.6 g) in absolute ethanol (50 mL) was added 95% sodium methoxide (1.6 g), and the mixture was heated at reflux for 30 minutes. To the solution were added water (3.5 mL) and 85% potassium hydroxide (0.88 g), and the mixture was heated at reflux for 1 hour. After distilling off the solvent, the residue was poured into ice-water and washed with diethyl ether. It was adjusted to pH 2-3 with concentrated hydrochloric acid and the precipitated crystals were filtered, washed with water and dried to give 4.47 g of 2-[4-methyl-2-oxo-3-(thiophen-3-yl)-3-pyrrolin-1-yl]isobutyric acid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 30 minutes
  3. temperaturethe mixture was heated
  4. temperatureat reflux for 1 hour
  5. distillationAfter distilling off the solvent
  6. additionthe residue was poured into ice-water
  7. washwashed with diethyl ether
  8. filtrationthe precipitated crystals were filtered
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-21dde51d64a34676a666c93abe34ea2e
Source dataset
uspto-grants-1999_11
Patent number
US05977027

Reaction notes

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