Organic compounds -- part of the class 532-570 series – Organic compounds – Phosphorus acids or salts thereof
Patent
1998-05-20
2000-07-04
Killos, Pual J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Phosphorus acids or salts thereof
562 11, C07F 944
Patent
active
060841230
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
This invention relates to a process for the preparation of an optically active 1-aminophosphonic acid derivative with using a catalyst for asymmetric synthesis of said derivative. This invention also relates to a method for the preparation of a novel catalyst for use in an asymmetric synthesis in the above process. Furthermore, this invention includes also a novel 1-aminophosphonate derivative obtained as intermediates in the above process.
BACKGROUND ART
It is known that a 1-aminoalkylphosphonic acid or its peptide-related derivatives have an antibacterial action against gram-positive bacteria and gram-negative bacteria and also can enhance the activity of some antibiotics such as penicillin, cephalosporin and D-cycloserine, that alaphospharine, which is a dipeptide obtained from L-alanine and L-aminoethylphosphonic acid, is especially important, and that in general, an optically active 1-aminoalkylphosphonic acid derivative and particularly its derivatives in the L-form (R-form) thereof can exhibit broad biological activities (Japanese patent application first publication "Kokai" No. 61-88895).
Such a process for obtaining the optically active 1-amino-alkylphosphonic acid, which comprise effecting an asymmetric synthesis thereof with using an enzyme, include methods described in the "Tetrahedron Asymmetry" Vol.4, p.1965 (1993) and Japanese patent application first publication "Kokai" No. 61-88895 and others.
For example, Japanese patent application first publication "Kokai" No. 61-88895 describes such a process for the preparation of an optically active stereoisomer of 1-aminoalkylphosphonic acid of the formula: ##STR2## where R.sup.2 represents, for example, a branched or preferably straight alkyl group of 1 to 6 carbon atoms, particularly 1 to 4 carbon atoms and optionally substituted with a halogen, hydroxyl group, alkoxy group of 1 to 3 carbon atoms, phenyl group and/or phenoxy group, or alternatively R.sup.2 represents a phenyl group, which process comprises effecting the optical resolution of the N-acyl derivative of a 1-aminoalkylphosphonic acid or a racemic mixture of the 1-aminoalkyl phosphonic acid with use of an enzyme, and then deacylating the resulting optically active N-acyl derivative to prepare the stereo-isomer, characterized in that the enzymatic, optical resolution is effected with penicillin-G-amidase. However, this enzymatic and asymmetric synthetic process has a problem that a scope of the substrate which can be used as the starting material is limited.
Furthermore, as such a process for preparation of the optically active 1-aminoalkylphosphonic acid which comprises effecting the asymmetric synthesis thereof without using the enzyme, there are hitherto known several processes which are described in the following literatures (1) to (4). Thus;
(1) there is known a process for effecting the optical resolution of a racemic mixture of 1-aminoalkylphosphonic acid with using anhydrous dibenzoyl-L-tartaric acid, wherein the target optically active .alpha.-aminoalkylphosphonic acid is obtained in a yield of 70 to 87% (Canadian Journal of Chemical Engineering, Vol.61, p.2425, 1983);
(2) there is known a process for the preparation of optically active 1-aminoalkylphosphonic acid which comprises effecting asymmetric alkylation to give an optically active aminoalkylphosphonic acid ester, wherein the target substance is obtained in a yield of 50 to 86% and at an optical purity of 25 to 76% (Tetrahedron Letters, Vol.33, p.6127, 1992);
(3) there is known a process for the preparation of optically active 1-aminoalkylphosphonic acid which comprises effecting a diastereo-selective addition reaction of phosphonic acid ester to an optically active imine, wherein the target substance is obtained in a yield of 30 to 90% and at an optical purity of 71 to 99% (The Journal of American Chemical Society, Vol.116, p.9377, 1994); and
(4) there is known a process for the preparation of optically active .alpha.-aminoalkylphosphonic acid which comprises effecting an asymmetric hydrogenation reac
REFERENCES:
patent: 4098849 (1978-07-01), Redmore
patent: 4235809 (1980-11-01), Redmore
patent: 4442286 (1984-04-01), Redmore
patent: 4804500 (1989-02-01), Miller
"Catalytic Asymmteric Synthesis of .sup..alpha. .sup.-Amino Phosphonates Using Lanthanoid-Potassium-BINOL Complexes", by H. Sasai et al., J. Org. Chem., vol. 60, No. 21, Oct. 20, 1995, pp. 6656-6657.
"Synthesis of 1-aminoalkane phosponic acids via benzhydrylic Schiff bases" by I. Kurt, et al., Chemical Abstracts 96:104372w vol. 96, 1992 p. 721.
Sasai Hiroaki
Shibasaki Masakatsu
Tahara Yoshihiro
Hokko Chemical Industry Co. Ltd.
Killos Pual J.
Vollano Jean F
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