Sodium Hydroxide → HCID 22851698, compound

HRID 1033843Notes

Reaction equation

HRID 1033843 reaction equation
[NH2:1][C@H:2]1[C@H:7]([C:8]([OH:10])=[O:9])[C@@H:6]([CH3:11])[O:5][C:3]1=[O:4].[OH-:12].[Na+]>CO>[NH2:1][C@@H:2]([C@H:7]([C:8]([OH:10])=[O:9])[C@H:6]([OH:5])[CH3:11])[C:3]([OH:12])=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22851699HCID 22851699, compound

Product 1

HCID 22851698HCID 22851698, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.07 g of 2(S)-amino-3(S)-carboxy-4(R)-pentanolide are suspended in 10 ml of methanol and dissolved by the addition of 13 ml of 2N aqueous sodium hydroxide solution with stirring at room temperature. The solvent mixture is distilled off and acetonitrile is added to the oily residue. The crystals which gradually form are filtered off, washed with a small amount of acetonitrile and dried under a high vacuum. The disodium salt of the title compound remains behind, [α]D20 =-9.0° (1% in water). 1H-NMR (D2O): 1.21 (3H, d 6.4 Hz), 2.54 (1H, dxd 6.4 and 8.4 Hz), 3.49 (1H, d 6 Hz), 3.97 (1H, dxq 8.4 and 6.4 Hz).

Workup

  1. distillationThe solvent mixture is distilled off
  2. additionacetonitrile is added to the oily residue
  3. filtrationThe crystals which gradually form are filtered off
  4. washwashed with a small amount of acetonitrile
  5. customdried under a high vacuum
  6. custom[α]D20 =-9.0° (1% in water)

Sources & evidence

ORD record
ord-bfe36adfb5e640fa900e1911fd9252b5
Source dataset
uspto-grants-1994_05
Patent number
US05312914

Reaction notes

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