Process for preparing N-benzyloxycarbonyl-L-aspartic acid

Details Process for preparing N-benzyloxycarbonyl-L-aspartic acid Process for preparing N-benzyloxycarbonyl-L-aspartic acid

1983-08-26

1985-05-21

Shippen, Michael L.

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

Organic compounds

Carboxylic acid esters

C07C125065

Patent

active

045187924

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 temperatures from about 5.degree.-55.degree. C. and over a wide pH range of about 9.2 to 13.8 in the presence of a surfactant and/or a buffer and then acidifying the reaction mixture. Carrying out the reaction in the presence of a surfactant reduces cycle time, while maintaining a high yield with low by-product content. The buffer prevents wide fluctuations in pH and minimizes localized reaction. These conditions are desirable when the reaction rate has been increased by addition of a surfactant or an increase in temperature of the reaction mixture.

REFERENCES:
patent: 3808190 (1974-04-01), Dahlmans
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," pp. 10-60 to 10-62, (1979), 12th Ed.
McCutcheon, "Synthetic Detergents," pp. 255, 273 & 384, (1950).
Schwartz, "Surface Active Agents," vol. 1, 3-21, 513-4, (1949).

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