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

1993-05-18

1994-06-07

Brust, Joseph Paul

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D20708

Patent

active

053190980

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 pyruvylproline 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: 4868312 (1989-09-01), Maeda et al.
patent: 4943640 (1990-07-01), Woo et al.
Blacklock, et al., J. Org. Chem., 53(1988), pp. 836-841.

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