Synthesis of N-benzyloxycarbonyl-L-aspartic acid

Details Synthesis of N-benzyloxycarbonyl-L-aspartic acid Synthesis of N-benzyloxycarbonyl-L-aspartic acid

1983-08-26

1985-06-11

Shippen, Michael L.

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

Organic compounds

Carboxylic acid esters

C07C125065

Patent

active

045230269

ABSTRACT:
N-Benzyloxycarbonyl-L-aspartic acid (Z-Asp) is synthesized by adding benzyl chloroformate to a solution of L-aspartic acid and sodium hydroxide at relatively high temperatures of 35.degree.-55.degree. C. and over a wide pH range of 9.2-12.0 and acidifying the sodium salt product. The Z-Asp is prepared in high yields exceeding 90% and purity of better than 99% with only a minor amount of the by-product N-benzyloxycarbonyl aspartyl aspartic acid. The Z-Asp is suitable for conversion to aspartame. Carrying out the reaction at high temperatures significantly reduces cycle time while maintaining a high yield with a low dipeptide and unreacted L-aspartic acid content.

REFERENCES:
patent: 3808190 (1974-04-01), Puhlmans
patent: 4293706 (1981-10-01), Gorman
patent: 4345091 (1982-08-01), Sugiyama
Roberts, "An Introduction to Modern Experimental Organic Chemistry," pp. 152-158 (1969).
Mortimer, "Chemistry a Conceptual Approach, " pp. 469-473 (1967).
Greenstein, "Chemistry of the Amino Acids," vol. 2, pp. 887-901 (1961).
Dean, "Lange's Handbook of Chemistry, " 12th Ed., pp. 10-60 to 10-62 (1979).

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