Sodium Hydroxide → HCID 11020616, compound

HRID 1707363Notes

Reaction equation

HRID 1707363 reaction equation
[C:1]([O:6][CH:7]1[CH:11]([CH2:12][CH:13]([CH3:15])[CH3:14])[NH:10][C:9](=[O:16])[CH2:8]1)(=[O:5])[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>O>[C:1]([O:6][C@@H:7]1[C@H:11]([CH2:12][CH:13]([CH3:15])[CH3:14])[NH:10][C:9](=[O:16])[CH2:8]1)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18963415HCID 18963415, compound

Product 1

HCID 11020616HCID 11020616, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

20 g of (4RS,5RS)-4-butyryloxy-5-isobutylpyrrolidin-2-one (produced according to Example 4) and 2 g of Candida cylindracea lipase (Biocatalysts) were stirred in 100 ml of water at room temperature. The pH of the suspension was held constant at 7 by the addition of 1M sodium hydroxide solution. After 70 hours and a consumption of 47.36 ml of 1M sodium hydroxide solution (corresponding to 53.8 percent conversion), the reaction was terminated. The reaction mixture was diluted with 200 ml of water and extracted once with 400 ml and another two times with 200 ml of toluene each. The combined toluene phases were concentrated by evaporation in a vacuum and the residue was dried in a high vacuum. The yield of the title compound was 8.55 g (85.5 percent, relative to one enantiomer). The title compound had a melting point of 94.9° to 95.3° C. Other data concerning the title compound was:

Workup

  1. customa consumption of 47.36 ml of 1M sodium hydroxide solution (corresponding to 53.8 percent conversion)
  2. customthe reaction was terminated
  3. additionThe reaction mixture was diluted with 200 ml of water
  4. extractionextracted once with 400 ml
  5. concentrationThe combined toluene phases were concentrated by evaporation in a vacuum
  6. customthe residue was dried in a high vacuum

Sources & evidence

ORD record
ord-0597e7ad646449d69d772f75f2bdb91a
Source dataset
uspto-grants-1994_10
Patent number
US05352801

Reaction notes

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