Sodium Methoxide → {2-[2-({2-[2-(3,4,5,6,7-Pentahydroxy-2-oxoheptyloxy)ethoxy]ethylcarbamoyl]methoxy)ethoxy]ethoxy}acetic acid

HRID 2104904Notes

Reaction equation

HRID 2104904 reaction equation
C[O-].[Na+].C([O:7][CH:8]([CH:33]([O:46]C(=O)C)[CH:34]([O:42]C(=O)C)[CH:35]([O:38]C(=O)C)[CH2:36][OH:37])[C:9](=[O:32])[CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][NH:17][C:18]([CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][C:29]([OH:31])=[O:30])=[O:19])(=O)C>CO>[OH:7][CH:8]([CH:33]([OH:46])[CH:34]([OH:42])[CH:35]([OH:38])[CH2:36][OH:37])[C:9](=[O:32])[CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][NH:17][C:18]([CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][C:29]([OH:31])=[O:30])=[O:19]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 22252083{2-[2-({2-[2-(3,4,5,6-Tetraacetoxy-7-hydroxy-2-oxo-heptyloxy)ethoxy]ethylcarbamoyl}methoxy)ethoxy]ethoxy}acetic acid

Product 1

HCID 22252092{2-[2-({2-[2-(3,4,5,6,7-Pentahydroxy-2-oxoheptyloxy)ethoxy]ethylcarbamoyl]methoxy)ethoxy]ethoxy}acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

At room temperature, 100 μl of a 5.4 M sodium methoxide solution in methanol are added to a solution of 200 mg of {2-[2-({2-[2-(3,4,5,6-tetraacetoxy-7-hydroxy-2-oxo-heptyloxy)ethoxy]ethylcarbamoyl}methoxy)ethoxy]ethoxy}acetic acid (24) in 5 ml of methanol, and the mixture is stirred for 2 h. 1 g of Amberlite IR 120 is added to the reaction solution and the mixture is stirred for 10 min, filtered and concentrated, giving 26:

Workup

  1. addition1 g of Amberlite IR 120 is added to the reaction solution
  2. stirringthe mixture is stirred for 10 min
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5b5480c1c60448118764e761c3ac78e9
Source dataset
uspto-grants-2009_08
Patent number
US07576200B2

Reaction notes

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