Citric Acid → gamma-Carboxyglutamic acid

HRID 373623노트

반응식

HRID 373623 반응식
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]

참가 물질

4

반응물 3

HCID 311Citric AcidHCID 8857Ethyl AcetateHCID 3034034Quinine

생성물 1

HCID 104625gamma-Carboxyglutamic acid

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-c28b411020444f37b7af74276db32d7c
출처 데이터셋
uspto-grants-1992_11
특허 번호
US05164483

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