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

HRID 6661

Reaction equation

HRID 6661 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-7b901fc15a6e4f8abc6c1204b5292bcc
Source dataset
uspto-grants-2006_08
Patent number
US07084123B2

Linked notes

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