Method for preparing amino acid ester hydrohalides

Details Method for preparing amino acid ester hydrohalides Method for preparing amino acid ester hydrohalides

1984-08-31

1986-11-11

Trousof, Natalie

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

Organic compounds

Carboxylic acid esters

546335, 548344, 548491, 548532, 548535, 560 40, 560153, 560155, 560168, 560169, 560170, 560171, 560173, C07C 6708

Patent

active

046224130

ABSTRACT:
Amino acid ester hydrohalide is produced by reacting amino acid, alcohol, and halocarbonyl compound represented by the formula: ##STR1## in the presence of an excess of the alcohol and under substantially anhydrous conditions, wherein X.sub.1 and X.sub.2 are each independently fluoro, chloro, bromo, trichloromethoxy or tribromomethoxy.

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Brenner et al, Chemical Abstracts, vol. 51, No. 4278a, (1957).
Greenstein et al, Chemistry of the Amino Acids, reprinted ed., Robt. E. Krieger Pub. Co., Malabar, Florida, pp. 860-876, 1278-1281, (1984).
Bodanszky, Principals of Peptide Synthesis, Springer-Verlag, Berlin, pp. 24-26, (1984).
Fieser et al, Reagents for Organic Synthesis, vol. 1, pp. 856, 858-859, (1967).
Iwakura et al, "Benzyl Esters of .alpha.-Amino Acids", Bulletin of the Chemical Society of Japan, vol. 37, pp. 1707-1709 (1964).
Matzner et al, "The Chemistry of Chloroformates", Chemical Reviews, vol. 64, pp. 654-655 and 677-684 (1964).
Domagala, "A Mild, Rapid, and Convenient Esterification of .alpha.-Keto Acids", Tetrahedron Letters, vol. 21, pp. 4997-5000 (1980).
Kim et al, "A New Convenient Method for the Esterification of Carboxylic Acids", Tetrahedron Letters, vol. 24, No. 32, pp. 3365-3368 (1983).

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