Sodium Carbonate → {2-[2-(2,3,4,5,6-Pentahydroxyhexanoylamino)ethoxy]ethoxy}acetic acid

HRID 2104898Notes

Reaction equation

HRID 2104898 reaction equation
[C:1](=O)([O-])[O-:2].[Na+].[Na+].[NH2:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][C:15]([OH:17])=[O:16].[OH:18][C:19]1([CH2:28][OH:29])[CH:24]([OH:25])[CH:23]([OH:26])[CH2:22][O:21]C1=O>CO>[OH:29][CH:28]([CH:19]([OH:18])[CH:24]([OH:25])[CH:23]([OH:26])[CH2:22][OH:21])[C:1]([NH:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][C:15]([OH:17])=[O:16])=[O:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 362706(2-(2-Aminoethoxy)ethoxy)acetic acidHCID 690616063,4,5-Trihydroxy-hydroxymethyltetrahydropyran-2-one

Product 1

HCID 22252087{2-[2-(2,3,4,5,6-Pentahydroxyhexanoylamino)ethoxy]ethoxy}acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

172 mg of sodium carbonate are added to a solution of 450 mg of [2-(2-aminoethoxy)ethoxy]acetic acid and 318 mg of 3,4,5-trihydroxy-hydroxymethyltetrahydropyran-2-one in 10 ml of methanol, and the mixture is stirred at room temperature until the reaction has gone to completion. The reaction solution is filtered and concentrated. The residue is taken up in water and acetonitrile (1/1), resulting in the formation of 2 phases. The aqueous phase is concentrated and contains 20:

Workup

  1. filtrationThe reaction solution is filtered
  2. concentrationconcentrated
  3. customacetonitrile (1/1), resulting in the formation of 2 phases
  4. concentrationThe aqueous phase is concentrated

Sources & evidence

ORD record
ord-18916e3db3914fb7851d79ccd68b45b3
Source dataset
uspto-grants-2009_08
Patent number
US07576200B2

Reaction notes

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