Sodium Hydroxide → HCID 67459886, compound

HRID 554120Notes

Reaction equation

HRID 554120 reaction equation
[CH:1]1([N:6]2[C:14](=[O:15])[CH2:13][CH2:12][C@H:7]2[C:8]([O:10]C)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C>[CH:1]1([N:6]2[C:14](=[O:15])[CH2:13][CH2:12][C@H:7]2[C:8]([OH:10])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67460760HCID 67460760, compound

Product 1

HCID 67459886HCID 67459886, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 1-cyclopentyl-5-oxoprolinate (0.560 g, 2.65 mmol) was dissolved in ethanol (10 ml) and cooled to 0° C. in an ice-bath. 2M aqueous sodium hydroxide (5 ml) was added and the mixture was stirred at ice temperature for 4 hrs. The ethanol was then evaporated under vacuum and the aqueous residue was acidified to pH1 by the addition of 2N aqueous hydrogen chloride. The volume of resulting aqueous mixture was reduced under vacuum to ˜3 ml and this was then extracted with a 3:1 mixture of chloroform and isopropanol respectively using a phase separator. The aqueous layer was washed with more dichloromethane and then the combined organic fractions were evaporated to give crude 1-cyclopentyl-5-oxoproline which was used in subsequent reactions without further purification.

Workup

  1. customThe ethanol was then evaporated under vacuum
  2. additionthe aqueous residue was acidified to pH1 by the addition of 2N aqueous hydrogen chloride
  3. extractionthis was then extracted with a 3:1 mixture of chloroform and isopropanol
  4. washThe aqueous layer was washed with more dichloromethane
  5. customthe combined organic fractions were evaporated

Sources & evidence

ORD record
ord-3dae6ba1383040999ce985bdc905b22e
Source dataset
uspto-grants-2011_11
Patent number
US08048907B2

Reaction notes

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