Aldono-1,5-lactone → {2-[2-(2,3,4,5,6-Pentahydroxyhexanoylamino)ethoxy]ethoxy}acetic acid

HRID 1725280Notes

Reaction equation

HRID 1725280 reaction equation
C(=O)([O-])[O-].[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][CH:19]1[CH:24]([OH:25])[CH:23]([OH:26])[CH:22]([CH2:27][OH:28])[O:21][C:20]1=[O:29]>CO>[OH:21][CH:22]([CH:23]([OH:26])[CH:24]([OH:25])[CH:19]([OH:18])[CH2:20][OH:29])[C:27]([NH:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][C:15]([OH:17])=[O:16])=[O:28]

Participants

5

Reactant 3

HCID 736Aldono-1,5-lactoneHCID 10340Sodium CarbonateHCID 362706(2-(2-Aminoethoxy)ethoxy)acetic acid

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-6-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-777cbe4bc57f40859809cec5cbd3d568
Source dataset
uspto-grants-2009_02
Patent number
US07488829B2

Reaction notes

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