Tallinn University of Technology

Cambrex Tallinn As

Anne Paju

Margus Lopp

Marit Laos

Margus Eek

Tonis Pehk

Katharina Matkevits

Raissa Jaalaid

The invention relates to the method of preparation of compounds of formula I, the precursors of homocitric acid lactone and its salts, by coupling of the compounds of formula II with bromoacetic acid esters of formula III. 

Method for preparation of (2-hydroxy-3-oxo-cyclopent-1-enyl)-acetic acid esters

Archiral (2-hydroxy-3-oxo-cyclopent-1-enyl) acetic acid) alkyl, alkylphenyl and phenyl esters, and a simple and efficient method for the synthesis of both enantiomers of homocitric acid gamma-lactone and the corresponding salts from these esters are described. The method is based on asymmetric oxidation of esters, and the steps of basic and acidic hydrolysis and final acidic lactonization of the homocitric acid into homocitric acid gamma-lactone. The homocitric acid salts are obtained after basic treatment of homocitric acid gamma-lactone. The esters, conditions and reagents used in chemical conversion and separating products are important constituents affording efficient and simple method for production of homocitric acid gamma-lactone and homocitric acid salts.

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Tallinn, Estonia

Anne Paju