Citric Acid → gamma-Carboxyglutamic acid

HRID 373623Notes

Reaction equation

HRID 373623 reaction equation
COC1C=CC2[N:12]=CC=C([C@@H](O)[C@H]3N4C[C@H](C=C)[C@@H](CC4)C3)C=2C=1.[C:25]([OH:37])(=[O:36])[CH2:26][C:27]([CH2:32][C:33]([OH:35])=[O:34])(C(O)=O)O.[C:38]([O:41]CC)(=[O:40])C>>[C:38]([CH:32]([C:33]([OH:35])=[O:34])[CH2:27][C@@H:26]([C:25]([OH:37])=[O:36])[NH2:12])([OH:41])=[O:40]

Participants

4

Reactant 3

HCID 311Citric AcidHCID 8857Ethyl AcetateHCID 3034034Quinine

Product 1

HCID 104625gamma-Carboxyglutamic acid

Procedure

The quinine salt of the optically active isomer (II) obtained in the above Example 1 (46.8 mg) was suspended in ethyl acetate and desalted with 1 N citric acid. The organic layer was washed with saturated aqueous sodium chloride and dried. Evaporation of ethyl acetate under reduced pressure gave 27.5 mg of a free γ-carboxyglutamic acid derivative (hereinafter called sample (a)). Its whole amount was dissolved in 2.8 ml of dichloromethane and to the resultant solution were added 14.2 mg of 2-chloro-1-methylpyridinium, 8.2 μl of R-(+)-1-(α-naphthyl)ethylamine and 26.6 μl of n-butylamine, and the reaction was carried out at 40° C. for 2 hours. After completion of the reaction, diastereomer fractions formed by thin layer chromatography were separated. The fractions were eluted with ethyl acetate, and then the residue obtained by evaporation under reduced pressure was analyzed by high performance liquid chromatography under the following conditions.

Workup

  1. washThe organic layer was washed with saturated aqueous sodium chloride
  2. customdried
  3. customEvaporation of ethyl acetate under reduced pressure

Sources & evidence

ORD record
ord-c28b411020444f37b7af74276db32d7c
Source dataset
uspto-grants-1992_11
Patent number
US05164483

Reaction notes

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