Citric Acid → 1-ethoxycarbonyl-3-(6-O-ethoxycarbonyl-beta-D-glucopyranosyl-oxy)-4-[(4-ethylthiophenyl)methyl]-5-methylpyrazole

HRID 33134

반응식

HRID 33134 반응식
[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[C:12]([O:17][C@@H:18]3[O:26][C@H:25]([CH2:27][OH:28])[C@@H:23]([OH:24])[C@H:21]([OH:22])[C@H:19]3[OH:20])=[N:13][NH:14][C:15]=2[CH3:16])=[CH:6][CH:5]=1)[CH3:2].Cl[C:30]([O:32][CH2:33][CH3:34])=[O:31].[C:35]([OH:47])(=[O:46])CC(CC(O)=O)(C(O)=O)O.[CH3:48][C:49]1C=C(C)C=C(C)N=1>>[CH2:33]([O:32][C:30]([N:14]1[C:15]([CH3:16])=[C:11]([CH2:10][C:7]2[CH:8]=[CH:9][C:4]([S:3][CH2:1][CH3:2])=[CH:5][CH:6]=2)[C:12]([O:17][C@@H:18]2[O:26][C@H:25]([CH2:27][O:28][C:35]([O:47][CH2:48][CH3:49])=[O:46])[C@@H:23]([OH:24])[C@H:21]([OH:22])[C@H:19]2[OH:20])=[N:13]1)=[O:31])[CH3:34]

참가 물질

5

반응물 4

HCID 311Citric AcidHCID 79532,4,6-TrimethylpyridineHCID 10928Ethyl chloroformateHCID 673371464-[(4-ethylthiophenyl)methyl]-3-(beta-D-glucopyranosyloxy)-5-methyl-1H-pyrazole

생성물 1

HCID 235431661-ethoxycarbonyl-3-(6-O-ethoxycarbonyl-beta-D-glucopyranosyl-oxy)-4-[(4-ethylthiophenyl)methyl]-5-methylpyrazole

실험 절차

To a solution of 4-[(4-ethylthiophenyl)methyl]-3-(β-D-glucopyranosyloxy)-5-methyl-1H-pyrazole (0.03 g) in 2,4,6-trimethylpyridine (0.5 mL) was added ethyl chloroformate (0.021 mL), and the mixture was stirred at room temperature overnight. To the reaction mixture was added 10% aqueous citric acid solution, and the resulting mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by preparative thin layer chromatography on silica gel (eluent: dichloromethane/methanol=10/1) to give 1-ethoxycarbonyl-3-(6-O-ethoxycarbonyl-β-D-glucopyranosyl-oxy)-4-[(4-ethylthiophenyl)methyl]-5-methylpyrazole (0.023 g).

후처리

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was purified by preparative thin layer chromatography on silica gel (eluent: dichloromethane/methanol=10/1)

출처 및 근거

ORD 기록
ord-94f17b236baf4c77bf9bbd5c6655c810
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429568B2

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