Acetic Anhydride → HCID 19805000, compound

HRID 728876Notes

Reaction equation

HRID 728876 reaction equation
C(=O)([O-])O.[Na+].[C:6](OC(=O)C)(=[O:8])[CH3:7].[NH2:13][CH:14](/[CH:18]=[CH:19]/[CH2:20][P:21]([OH:24])([OH:23])=[O:22])[C:15]([OH:17])=[O:16]>O1CCOCC1.O>[NH:13]([CH:14](/[CH:18]=[CH:19]/[CH2:20][P:21]([OH:24])([OH:23])=[O:22])[C:15]([OH:17])=[O:16])[C:6]([CH3:7])=[O:8]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 6506250HCID 6506250, compound

Product 1

HCID 19805000HCID 19805000, compound

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

At 0°, 170 mg of sodium hydrogen carbonate and, within a period of 5minutes, 50 microliters of acetic anhydride are added to a solution of 100 mg of E-2-amino-5-phosphono-3-pentenoic acid in 6 ml of dioxan/water (1:1). The whole is stirred for 30 minutes at 0°, approximately 2 ml of Dowex 50 H+ are added and filtration is carried out. The filtrate is concentrated by evaporation and purified by ion exchange chromatography (Dowex 50 H+). Lyophilisation of the pure fractions yields 110 mg of E-2-acetamino-5-phosphono-3-pentenoic acid, m.p. 155°.

Workup

  1. additionapproximately 2 ml of Dowex 50 H+ are added
  2. filtrationfiltration
  3. concentrationThe filtrate is concentrated by evaporation
  4. custompurified by ion exchange chromatography (Dowex 50 H+)

Sources & evidence

ORD record
ord-cb8ddd8849f84789aec7c5a46553fe2a
Source dataset
uspto-grants-1991_09
Patent number
US05051413

Reaction notes

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