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

HRID 6660

反応式

HRID 6660 の反応式
[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]

参加物

5

反応物 4

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

生成物 1

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

実験手順

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 ethylacetate. 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-glucopyranosyloxy)-4-[(4-ethylthiophenyl)methyl]-5-methylpyrazole (0.023 g).

後処理

  1. extractionthe resulting mixture was extracted with ethylacetate
  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)

出典と根拠

ORDレコード
ord-ecce5c467964454bbe231535179e1e69
出典データセット
uspto-grants-2006_08
特許番号
US07084123B2

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