Abstract
A. L. LEVY1 has described the preparation of anhydro-N-carboxy-DL-β-phenylalanine (II, R=CH2Ph) by the action of phosgene on DL-β-phenylalanine. Prior to this, Fuchs2 described the preparation of anhydro-N-carboxy-N-phenyl- and N-p-tolyl-glycine by phosgenation of the parent acids in aqueous solution. Isatoic anhydride3, the analogous compound from anthranilic acid, has been similarly prepared. A modified method based on this reaction of Fuchs has been used recently by several workers in these laboratories. The process, which is fairly generally applicable and has been protected by a patent application4, consists of suspending the powdered α-amino-acid in a dry inert solvent, for example, dioxan or tetrahydrofuran, at 30°–40° and passing in gaseous phosgene with stirring until the acid is dissolved. Removal of solvent and excess phosgene by heating in vacuo at 40° then affords the anhydro-N-carboxy derivative (II), the intermediate N- substituted carbamyl chloride (I) being decomposed with the loss of hydrochloric acid during the treatment:
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References
Levy, A. L., Nature, 165, 152 (1950).
Fuchs, F., Ber., 55, 2943 (1922).
“Org. Syntheses”, 27, 45 (1947).
Baird, W., Parry, E. G., Robinson, S., and Imperial Chemical Industries, Ltd., Brit. Pat. Appl. 20406/47 (29.7.47).
Brown, C. J., Coleman, D., and Farthing, A. C., Nature, 163, 834 (1949).
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FARTHING, A., REYNOLDS, R. Anhydro-N-Carboxy-DL-β-Phenylalanine. Nature 165, 647 (1950). https://doi.org/10.1038/165647a0
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DOI: https://doi.org/10.1038/165647a0
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