Sodium Hydroxide → HCID 22851698, compound

HRID 55462Notes

Reaction equation

HRID 55462 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-f3d76ff78a1d49d78bb0dc409b311591
Source dataset
uspto-grants-1997_04
Patent number
US05625059

Reaction notes

Loading…