Sodium Hydroxide → HCID 67459915, compound

HRID 554090Notes

Reaction equation

HRID 554090 reaction equation
[CH2:1]([N:3]1[C:11](=[O:12])[CH:10]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][C@H:4]1[C:5]([O:7]C)=[O:6])[CH3:2].[OH-].[Na+]>CO>[CH2:1]([N:3]1[C:11](=[O:12])[CH:10]([CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:9][C@H:4]1[C:5]([OH:7])=[O:6])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67460655HCID 67460655, compound

Product 1

HCID 67459915HCID 67459915, compoundYield 233.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 1-ethyl-5-oxo-4-(phenylmethyl)-prolinate (0.024 g, 0.09 mmol) was dissolved in methanol (0.5 ml) and cooled to 0° C. in an ice-bath. 2M aqueous sodium hydroxide (0.137 ml, 0.27 mmol) was added to the mixture and stirring continued at 0° C. for 3 hrs. The solvent was evaporated and the residue was acidified by treatment with 2M aqueous hydrogen chloride (˜0.2 ml) to give a cloudy solution. Evaporation then gave crude 1-ethyl-5-oxo-4-(phenylmethyl)-proline (0.052 g) as a mixture of white solids and yellow oily residues. This was used without further purification.

Workup

  1. customThe solvent was evaporated
  2. customto give a cloudy solution
  3. customEvaporation

Sources & evidence

ORD record
ord-3b5b26c448f447a0a0434ff34b7035f3
Source dataset
uspto-grants-2011_11
Patent number
US08048907B2

Reaction notes

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