Synthesis of l-azatyrosine using pseudoephedrine as a chiral aux

Details Synthesis of l-azatyrosine using pseudoephedrine as a chiral aux Synthesis of l-azatyrosine using pseudoephedrine as a chiral aux

1995-08-25

1998-06-02

Ivy, C. Warren

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

514351, 546312, C07D21316, A61K 3144

Patent

active

057602379

ABSTRACT:
A practical synthesis of the potential chemotherapeutic agent L-azatyrosine is described. The key step involved the alkylation of (R,R)-(-)-pseudoephedrine glycinamide with 5-benzenesulfonyloxy-2-iodomethylpyridine and proceeded in 70-95% yield and 89-95% de. Simultaneous hydrolysis of the auxiliary and the benzenesulfonate protecting group afforded L-azatyrosine of .gtoreq.99% ee in 73% yield on multigram scale (recovery yield of (R,R)-(-)-pseudoephedrine: 90%).

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