Method for preparing (αS,5S)-α-amino-3-chloro-2-isoxazoline-5-acetic acid (AT-125) and analogs thereof

Claim 1

A process for preparing racemic mixtures and optically active isomers of a compound having the formula ##STR86## which comprises chlorinating a compound having the formula ##STR87## wherein R is selected from the group consisting of hydrogen, alkyl of from 1 to 8 carbon atoms, inclusive, halogenated alkyl of from 1 to 3 halogen atoms, and 1 to 5 carbon atoms, inclusive and aralkyl of from 7 to 20 carbon atoms, inclusive and substituted aralkyl of from 7 to 20 carbon atoms, inclusive; and R 14 and R 15 are selected from the group consisting of hydrogen, ##STR88## inclusive, or when taken together with the nitrogen atom form the group ##STR89## wherein R 6 is alkyl of from 1 to 8 carbon atoms, inclusive, halogenated alkyl of from 1 to 5 carbon atoms, inclusive, and 1 to 3 halogen atoms, inclusive, aralkyl of from 7 to 20 carbon atoms, inclusive, and substituted aralkyl of from 7 to 20 carbon atoms, inclusive, R 7 is selected from the group consisting of alkyl of from 1 to 12 carbon atoms, inclusive, aryl of from 6 to 20 carbon atoms, inclusive, aryl of from 6 to 20 carbon atoms, inclusive, aralkyl of from 7 to 20 carbon atoms, inclusive, substituted aralkyl of from 7 to 20 carbon atoms, inclusive, and R 8 is selected from the group consisting of ##STR90## where R 9 , R 10 , R 11 and R 12 are selected from the group consisting of hydrogen and alkyl of from 1 to 5 carbon atoms, inclusive, (b) ##STR91## (c) orthointerphenylene, and (d) substituted orthointerphenylene.