Process for producing 3-(3,4-dihydroxyphenyl) serine

Details Process for producing 3-(3,4-dihydroxyphenyl) serine Process for producing 3-(3,4-dihydroxyphenyl) serine

C - Chemistry, Metallurgy

07

D

260/516.3

C07D 209/48 (2006.01) C07D 317/60 (2006.01) C07D 405/12 (2006.01)

Patent

CA 1223602

ABSTRACT OF THE DISCLOSURE A process for producing racemic or optically active threo- or erythro-3-(3,4-dihydroxyphenyl)serine represented by the formula Image [I], which comprises phthaloylating the amine group of a racemic or optically active threo- or erythro-3-(3,4- dihydroxyphenyl)serine derivative represented by the general formula Image [IV] (wherein R1 and R2 each represents a hydrogen atom or a methyl group, or R1 and R2 jointly form a methylene group, provided that R1 and R2 do not simultaneously represent hydrogen atoms) to yield a racemic or optically active threo- or erythro-N-phthaloyl-3-(3,4-dihydroxy- phenyl)serine derivative represented by the general formula, [III] Image wherein R1 and R2 are as defined above; if necessary in the case in which the compound of formula [III] is in racemic form, subjecting the racemate to optical resolution through the reaction with one of the optically active amines to yield an optically active threo- or erythro-N-phthaloyl-3-(3,4-dihydroxyphenyl)serine derivative represented by the general formula [III]; treating the racemic or optically active threo- or erythro-N-phthaloyl-3-(3,4-dihydroxyphenyl)serine deri- vative represented by the above formula [III] with a Lewis acid to yield racemic or optically active threo- or erythro-N-phthaloyl-3-(3,4-dihydroxyphenyl-serine represented by the formula, Image [II]; \ if necessary in the case in which the compound of formula [II] is in racemic form, subjecting the racemate to optical resolution through the reaction with one of the optically active amines to yield an optically active threo- or erythro-N-phthaloyl-3-(3,4-dihydroxypheny)serine represented by the above formula [II], and removing the phthaloyl group from the racemic or optically active threo- or erythro-N-phthaloyl-3-(3,4-dihydroxyphenyl)- serine to yield the racemic or optically active threo- or erythro-3-(3,4-dihydroxyphenyl)serine represented by the above formula [I].

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