Synthesis of two cyclic analogs of glutamic acid: cis- and trans-pyrrolidine-2,4-dicarboxylic acids
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Add time:09/06/2019 Source:sciencedirect.com
The tosyl ester 2 of tetraethyl 1-acetamido-4-hydroxybutane- 1,1,3,3-tetracarboxylate gave 4-methylene glutammic acid in 90% yield by refluxing with concentrated HC1. Treatment of 2 with NaOEt, then with refluxing concentrated HC1 gave a 54% yield of cis and trans-pyrrolidine-2,4-dicarboxylic acids 4 and 5, separated by anion exchange chromatography An analytical resolution of 4 and 5 enantiomers by chiral derivatization and GPC is described.
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