Sodium Methoxide → HCID 68874371, compound

HRID 1982854Notes

Reaction equation

HRID 1982854 reaction equation
C([O:4][C@@H:5]1[C@@H:27]([O:28]C(=O)C)[C@H:26]([O:32]C(=O)C)[C@@H:25]([CH2:36][O:37]C(=O)C)[O:24][C@H:6]1[O:7][C:8]1[CH:13]=[C:12]([NH2:14])[CH:11]=[CH:10][C:9]=1[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH3:23])=[CH:18][CH:17]=1)(=O)C.C[O-].[Na+]>CO>[O:7]([C:8]1[CH:13]=[C:12]([NH2:14])[CH:11]=[CH:10][C:9]=1[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH3:23])=[CH:18][CH:17]=1)[C@@H:6]1[O:24][C@H:25]([CH2:36][OH:37])[C@@H:26]([OH:32])[C@H:27]([OH:28])[C@H:5]1[OH:4]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 68873213HCID 68873213, compound

Product 1

HCID 68874371HCID 68874371, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-amino-2-(4-ethylbenzyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (0.19 g) in methanol (3.5 mL) was added sodium methoxide (28% methanol solution; 0.064 mL), and the mixture was stirred at room temperature for 50 minutes. The reaction mixture was concentrated under reduced pressure, and to the residue was added water. Precipitated crystals were collected by filtration, washed with water and dried to give 5-amino-2-(4-ethylbenzyl)-phenyl β-D-glucopyranoside (0.12 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionto the residue was added water
  3. customPrecipitated crystals
  4. filtrationwere collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-f125ebcdc6234486a6874d3e9f0fea17
Source dataset
uspto-grants-2009_06
Patent number
US07541341B2

Reaction notes

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