Process for the stereoselective preparation of l-alanyl-l-prolin

Details Process for the stereoselective preparation of l-alanyl-l-prolin Process for the stereoselective preparation of l-alanyl-l-prolin

1994-05-26

1995-06-13

Brust, Joseph Paul

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D20712

Patent

active

054244544

ABSTRACT:
L-alanyl-L-proline is stereoselectively prepared catalytically hydrogenating an N-(2-iminopropionyl)-L-proline in the presence of a metal hydrogenolysis catalyst and at a pH of less than about 4. Also disclosed are improved processes for production of N-pyruvyl-L-proline in which L-proline and a 2,2-disubstituted propionyl halide are allowed to react at a pH of at least 9 to produce an L-proline intermediate which is hydrolyzed at a pH range of from about 6.5 to about 8.5 to yield N-pyruvyl-L-proline.

REFERENCES:
patent: 5319098 (1994-06-01), Burbaum et al.
Blacklock et al., "Synthesis of Semisynthetic Dipeptides Using N-Carboxyanhydrides and Chiral Induction on Raney Nickel. A Method Practical for Large Scale", J. Organic Chem., 53, pp. 836-844 (1988).
"Imidapril Hydrochloride", Drugs of the Future, Prous Science, 17(7), pp. 551-558 (1992).
Kleeman et al., Pharmazeutische Wirkstoffe, pp. 1154-1155 (1987).
Mukaiyama et al., "A Novel Method for the Preparation of Optically Active Dipeptide. Chemo-and Stereoselective Reduction of 2-Hydroxyimino Amides with Samarium Diiodide", Chemistry Letters, pp. 181-184 (1992).

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