Method for optical resolution of DL-cysteine and (R,S)-1-(1-naph

Details Method for optical resolution of DL-cysteine and (R,S)-1-(1-naph Method for optical resolution of DL-cysteine and (R,S)-1-(1-naph

1986-08-01

1988-04-05

Lone, Werren B.

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

Organic compounds

Carboxylic acids and salts thereof

562557, 548201, 564304, C07B 5700

Patent

active

047360607

ABSTRACT:
Method for optical resolution of DL-cysteine by (1) reacting DL-cysteine with formaldehyde to prepare DL-thiazolidine-4-carboxylic acid (DL-TCA), (2) forming diastereomer salts of D-TCA and of L-TCA by reacting DL-TCA with an optically active 1-(1-naphthyl)ethylamine, (3) separating said diastereomer salts by difference of the solubilities thereof in a solvent, (4) recovering D-TCA from said diastereomer salt of D-TCA and finally obtain D-cysteine, and recovering L-TCA from said diastereomer salt of L-TCA and finally obtain L-cysteine.
Method for optical resolution of (R,S)-1-(1-naphthyl)ethylamine (R,S)-NEA by (1) reacting an optically active cysteine with formaldehyde to prepare an optically active thiazolidine-4-carboxylic acid, (2) forming diastereomer salts of (R)-NEA and of (S)-NEA by reacting (R,S)-NEA with optically active thiazolidine-4-carboxylic acid, (3) separating said diastereomer salts of (R)-NEA and of (S)-NEA by difference of the solubilities thereof in a solvent, (4) recovering (R)-NEA from said diastereomer salt of (R)-NEA, and recovering (S)-NEA from said diastereomer salt of (S)-NEA.

REFERENCES:
patent: 3000947 (1961-09-01), Bottoms
patent: 3679694 (1972-07-01), Rambacher et al.
patent: 3808268 (1974-04-01), Rambacher et al.
patent: 4416828 (1983-11-01), Bethge et al.
patent: 4430509 (1984-02-01), Bethge et al.
patent: 4613688 (1986-09-01), Inoue et al.
patent: 4621151 (1986-11-01), Nohira et al.

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