Process for the resolution of DL-6-chlorotryptophan

Details Process for the resolution of DL-6-chlorotryptophan Process for the resolution of DL-6-chlorotryptophan

1976-04-29

1978-02-07

Love, Ethel G.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

C07D20920

Patent

active

040726916

ABSTRACT:
Seed crystals of one optically active enantiomer of 6-chlorotryptophan methanesulfonate or 6-chlorotryptophan benzenesulfonate are added to a supersaturated solution of DL-6-chlorotryptophan methanesulfonate or DL-6-chlorotryptophan benzenesulfonate. Crystallization of the optically active enantiomer results. The crystals are recovered. Alternatively, crystals of the optically active enantiomer may be added to a hot solution of DL-6-chlorotryptophan methanesulfonate or DL-6-chlorotryptophan benzenesulfonate to produce a supersaturated solution. The solution is then cooled to crystallize out the optically active enantiomer. Optically active 6-chlorotryptophan is prepared by treating optically active 6-chlorotryptophan methanesulfonate or 6-chlorotryptophan benzenesulfonate with an alkaline agent or an ion exchange resin.

REFERENCES:
patent: 2813876 (1957-11-01), Lyttle et al.
patent: 3149122 (1964-09-01), Sasaji et al.
patent: 3825559 (1974-07-01), Tazuke et al.
patent: 3904646 (1975-09-01), Chibata et al.
Shigeki et al., J. Agric. Food Chem. 23(4), 653-657 (1975).
Yamada et al., J. Org. Chem., vol. 38, No. 26, pp. 4408-4412 (1973).

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