Sodium Methoxide → HCID 68872109, compound

HRID 1826665Notes

Reaction equation

HRID 1826665 reaction equation
C([O:4][C@@H:5]1[C@@H:29]([O:30]C(=O)C)[C@H:28]([O:34]C(=O)C)[C@@H:27]([CH2:38][O:39]C(=O)C)[O:26][C@H:6]1[O:7][C:8]1[CH:13]=[C:12]([C:14](=[O:16])[NH2:15])[CH:11]=[CH:10][C:9]=1[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH3:25])=[CH:20][CH:19]=1)(=O)C.C[O-].[Na+]>CO>[O:7]([C:8]1[CH:13]=[C:12]([C:14](=[O:16])[NH2:15])[CH:11]=[CH:10][C:9]=1[CH2:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:24][CH3:25])=[CH:22][CH:23]=1)[C@@H:6]1[O:26][C@H:27]([CH2:38][OH:39])[C@@H:28]([OH:34])[C@H:29]([OH:30])[C@H:5]1[OH:4]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 68872276HCID 68872276, compound

Product 1

HCID 68872109HCID 68872109, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-carbamoyl-2-(4-ethylbenzyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (0.13 g) in methanol (3 mL) was added sodium methoxide (28% methanol solution, 0.043 mL), and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was purified by column chromatography on benzenesulfonylpropyl silica gel (eluent: methanol). Diethyl ether was added to the obtained compound, and the resulting precipitated solid was collected by filtration and dried under reduced pressure to give 5-carbamoyl-2-(4-ethylbenzyl)phenyl β-D-glucopyranoside (0.079 g).

Workup

  1. customThe reaction mixture was purified by column chromatography on benzenesulfonylpropyl silica gel (eluent: methanol)
  2. additionDiethyl ether was added to the obtained compound
  3. customthe resulting precipitated solid
  4. filtrationwas collected by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-f93a44db47364bed8ea050b367773ded
Source dataset
uspto-grants-2006_05
Patent number
US07053060B2

Reaction notes

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