تفاعل #6758

ord-e282bc156d3b4ff5858b7476742a21ad

معادلة التفاعل

O=C(O)CC(O)(CC(=O)O)C(=O)O
citric acid
CCSc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)nn(C(C)=O)c2C)cc1
1-acetyl-4-[(4-ethylthiophenyl)methyl]-3-(β-D-glucopyranosyloxy)-5-methylpyrazole
CCOC(=O)Cl
ethyl chloroformate
CCOC(=O)OC[C@H]1O[C@@H](Oc2nn(C(C)=O)c(C)c2Cc2ccc(SCC)cc2)[C@H](O)[C@@H](O)[C@@H]1O
1-acetyl-3-(6-O-ethoxycarbonyl-β-D-glucopyranosyloxy)-4-[(4-ethylthiophenyl)methyl]-5-methylpyrazole

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    workup.STIRRINGthe resulting mixture was stirred at room temperature overnight
  2. 2
    ترشيحThe resulting precipitatse were collected by filtration
  3. 3
    غسيلwashed with 10% aqueous citric acid solution and water

الإجراء التجريبي

To a solution of 1-acetyl-4-[(4-ethylthiophenyl)methyl]-3-(β-D-glucopyranosyloxy)-5-methylpyrazole (0.03 g) in 2,4,6-trimethylpyridine (0.5 mL) was added ethyl chloroformate (0.012 mL), and the mixture was stirred at room temperature overnight. To the reaction mixture was added 10% aqueous citric acid solution (5 mL), and the resulting mixture was stirred at room temperature overnight. The resulting precipitatse were collected by filtration and washed with 10% aqueous citric acid solution and water to give 1-acetyl-3-(6-O-ethoxycarbonyl-β-D-glucopyranosyloxy)-4-[(4-ethylthiophenyl)methyl]-5-methylpyrazole (0.020 g).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07084123B2uspto-grants-2006_08