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

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

1997-07-24

1999-01-26

Killos, Paul J.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548215, C07D26352

Patent

active

058640410

ABSTRACT:
Racemic or optically active threo-3-(3,4-dihydroxyphenyl)serine can be readily produced via a few short steps by a process involving the steps of reacting a racemic or optically active N-acyl DOPA derivative represented ##STR1## wherein X is a halogen atom; n is 0, 1, 2 or 3; R.sup.1 and R.sup.2 independently represent a protecting group for a hydroxyl group; R.sup.3 is a protecting group for carboxyl group; R.sup.4 is an alkyl group which may have a substituent or a phenyl group which may have a substituent; and a carbon marked with the symbol * is an asymmetric carbon, with a halogen radical generator, a cerium (IV) salt, or a persulfate salt in the presence of a copper catalyst to produce racemic or optically active ##STR2## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, X, n and * are as defined above; and thereafter conducting an oxazoline ring opening and removing R.sup.1, R.sup.2 and R.sup.3 and, optionally, removing X when n is 1, 2 or 3.

REFERENCES:
Shimamoto, K. & Ohfune, Y., A New Entry to the Synthesis of .beta.-Hydroxytyrosines Via a Novel Benzylic Hydroxylation, Tetrahedron Letters, vol. 29, No. 40, pp. 5177-5180, 1988.
Hayashi, T. & Sawamura, M. & Ito, Y., Asymmetric Synthesis Catalyzed by Chiral Ferrocenylphosphine-Transition Metal Complexes. 10.sup.1 Gold(I)-Catalyzed A symmetric Aldol Reaction of Isocyanoacetate, Tetrahedron, vol. 48, No. 11, pp. 1999-2012, 1992.
Chemical Abstracts 120:218452 & RN 154051-93-1, see abstract and compound in enclosed printout.
Chemical Abstracts 117:204212 & RNs 144125-91-7 & 144125-89-3, see abstract and compounds in enclosed printout.
Chemical Abstracts 113:132732 & RNs 129077-94-7 & 117831-96-6, see abstract and compound in enclosed printout.

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