Sodium Methoxide → HCID 68874371, compound

HRID 1247758Notes

Reaction equation

HRID 1247758 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 water was added to the residue. The resulting precipitated crystals were collected by filtration, washed with water and dried under reduced pressure to give 5-amino-2-(4-ethylbenzyl)phenyl β-D-glucopyranoside (0.12 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and water
  2. additionwas added to the residue
  3. customThe resulting precipitated crystals
  4. filtrationwere collected by filtration
  5. washwashed with water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-63354e61e44d4eedb7a90cc5a038f459
Source dataset
uspto-grants-2006_10
Patent number
US07129381B2

Reaction notes

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