Acetic Acid → 1-acetyl-4-[(4-ethylthiophenyl)-methyl]-3-(beta-D-glucopyranosyloxy)-5-methylpyrazole

HRID 746408

Reaktionsgleichung

Reaktionsgleichung von HRID 746408
[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].[C:29](O)(=[O:31])[CH3:30].C(OC(=O)C)(=O)C>O1CCCC1>[C:29]([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][OH:28])[C@@H:23]([OH:24])[C@H:21]([OH:22])[C@H:19]2[OH:20])=[N:13]1)(=[O:31])[CH3:30]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 673371464-[(4-ethylthiophenyl)methyl]-3-(beta-D-glucopyranosyloxy)-5-methyl-1H-pyrazole

Produkt 1

HCID 673357351-acetyl-4-[(4-ethylthiophenyl)-methyl]-3-(beta-D-glucopyranosyloxy)-5-methylpyrazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-[(4-ethylthiophenyl)methyl]-3-(β-D-glucopyranosyloxy)-5-methyl-1H-pyrazole (0.41 g) in tetrahydrofuran (10 mL) were added acetic acid (0.11 mL) and acetic anhydride (0.18 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and diethyl ether was added to the residue. The resulting precipitated crystal was collected by filtration to give 1-acetyl-4-[(4-ethylthiophenyl)methyl]-3-(β-D-glucopyranosyloxy)-5-methylpyrazole (0.36 g).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and diethyl ether
  2. additionwas added to the residue
  3. customThe resulting precipitated crystal
  4. filtrationwas collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-e0ab6a32e8ed4278a65d3db2b964f383
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07393838B2

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