Sodium Methoxide → 4-[4-(beta-D-glucopyranosyloxy)-phenyl]-2-(3,4-diethoxyphenyl)thiazole

HRID 1421961Notes

Reaction equation

HRID 1421961 reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@H:6]1[O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[N:32]=[C:33]([C:36]3[CH:41]=[CH:40][C:39]([O:42][CH2:43][CH3:44])=[C:38]([O:45][CH2:46][CH3:47])[CH:37]=3)[S:34][CH:35]=2)=[CH:27][CH:26]=1)(=O)C.C[O-].[Na+]>CO.ClCCl>[C@@H:6]1([O:24][C:25]2[CH:26]=[CH:27][C:28]([C:31]3[N:32]=[C:33]([C:36]4[CH:41]=[CH:40][C:39]([O:42][CH2:43][CH3:44])=[C:38]([O:45][CH2:46][CH3:47])[CH:37]=4)[S:34][CH:35]=3)=[CH:29][CH:30]=2)[O:7][C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]1[OH:4]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 540604894-[4-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)phenyl]-2-(3,4-diethoxyphenyl)-thiazole

Product 1

HCID 538041514-[4-(beta-D-glucopyranosyloxy)-phenyl]-2-(3,4-diethoxyphenyl)thiazoleYield 63.1%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

In 6 ml of a methanol-dichloromethane (2:1) mixed solvent was suspended 0.15 g of 4-[4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)phenyl]-2-(3,4-diethoxyphenyl)thiazole. Thereto was added a catalytic amount of sodium methylate. The mixture was stirred at room temperature for 2 hours. The solvent was removed by distillation. The residue was recrystallized from methanol to obtain 71 mg of 4-[4-(β-D-glucopyranosyloxy)phenyl]-2-(3,4-diethoxyphenyl)thiazole.

Workup

  1. customThe solvent was removed by distillation
  2. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-55cbe9d4f4e24189b7edad3c5ab4ffc2
Source dataset
uspto-grants-2000_06
Patent number
US06080764

Reaction notes

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