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

HRID 33135

Reaction equation

HRID 33135 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 tetra-hydrofuran (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-f1511d12fefe4bc2a6b3e2ecead97f28
Source dataset
uspto-grants-2008_09
Patent number
US07429568B2

Linked notes

Loading…