C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
C07D 303/40 (2006.01) C07C 269/06 (2006.01) C07C 269/08 (2006.01) C07C 271/16 (2006.01) C07C 319/28 (2006.01) C07C 323/43 (2006.01) C07D 263/24 (2006.01) C07D 303/36 (2006.01) C07D 303/46 (2006.01)
Patent
CA 2317198
The invention relates to a method of industrially producing (2R, 3S)- or (2S, 3R)-N-carbamate-protected .beta.- aminoepoxide in crystal form. The method of the invention comprises the steps of (a) dissolving a (2R, 3S)- or (2S, 3R)-N-carbamate-protected .beta.-aminoalcohol containing a diastereomer thereof as an impurity in at least one solvent selected from the group consisting of aromatic hydrocarbon solvents, aryl halide solvents, saturated hydrocarbon solvents, acetone, 2-propanol and mixtures of water-miscible organic solvents with water, to remove insoluble matters; (b) treating the (2R, 3S)- or (2S, 3R)-N-carbamate-protected .beta.-aminoalcohol with a base, thereby converting the N-carbamate-protected .beta.- aminoalcohol to a (2R, 3S)- or (2S, 3R)-N-carbamate- protected .beta.-aminoepoxide containing a diastereomer thereof as an impurity; (c) treating the (2R, 3S)- or (2S, 3R)-N-carbamate-protected .beta.-aminoepoxide containing the diastereomer as an impurity with an acid, thereby converting the diastereomer as an impurity to a (4S, 5R)- or (4R, 5S)-oxazolidin-2-one derivative; and (d) crystallizing the (2R, 3S)- or (2S, 3R)-N-carbamate- protected .beta.-aminoepoxide in a mixture of a water-miscible organic solvent with water.
Hirose Naoko
Honda Yutaka
Izawa Kunisuke
Nakano Takashi
Nakazawa Masakazu
Ajinomoto Co. Inc.
Ogilvy Renault Llp/s.e.n.c.r.l.,s.r.l.
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