Method of producing optically active 1,3-imidazolidine-4-ones

Details Method of producing optically active 1,3-imidazolidine-4-ones Method of producing optically active 1,3-imidazolidine-4-ones

1992-11-12

1995-01-31

Higel, Floyd D.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

5483241, 5483225, C07D23338, C07D23332, C07D23330, C07K 500

Patent

active

053860357

ABSTRACT:
2.2. 1,3-imidazolidine-4-ones having the General Formula: ##STR1## are obtained in a pure form especially by means of precipitation, in which production an optically active acid can be used at 0.5-0.8 eq. for the separation of racemates. The non-desired enantiomer can be racemized in an inert solvent and the cyclization to imidazolidinone can take place by means of the optically active acid, whereupon the separation of racemates takes place directly thereafter. 1,3-imidazolidine-4-ones are valuable educts for the preparation of branched or unbranched, proteinogenic or non-proteinogenic .alpha.-amino acids by means of diastereoselective alkylation and subsequent ring splitting.

REFERENCES:
patent: 4280008 (1981-07-01), Schoellkopf et al.
patent: 5210210 (1993-05-01), Davies
Naef et al, Helv. Chim Acta, vol. 68, pp. 135 to 143 (1985).
Angewandt Chemie, Bd. 98, Nr. 4, 1986, Weinheim pp. 363-364 Fitzi et al I.
Tetrahedron Bd. 44, Nr. 17, 1988, Great Britain pp. 5277-5292 Fitzi et al II "Resolution and use in alpha-amino acid synthesis of imidazolidinone glycine derivatives".
Liebigs Annalen Der Chemie 1989, Weinheim pp. 1215-1232; Dieter Seebach et al. III "Synthesis of Nonproteinogenic (R)-or (S)-Amino acids Analogues of Phenylalanine, . . . ".
Enantiomers, Racemates, and Resolutions by Jean Jacques and Andre Collet publication pp. 309-312 (1981).
Article entitled "Diastereoselective Cyclization of a Glycil-alanine Azomethine to an Imidazolidinone: Determination of the Product Configuration by X-Ray Analysis" 1989 by Martin Egli, Robin Polt and Dieter Seebach pp. 4 and 5.

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