Optically active imidazolidin-2-one derivatives

Details Optically active imidazolidin-2-one derivatives Optically active imidazolidin-2-one derivatives

1981-06-29

1983-09-06

Schwartz, Richard A.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548303, 548304, C07D23334

Patent

active

044030967

ABSTRACT:
A novel optically active cis-4,5-disubstituted imidazolidin-2-one derivative of the formula: ##STR1## wherein R.sup.1 is a C.sub.1 -C.sub.4 alkyl group or benzyl and R.sup.2 is a chiral aralkyl group optionally having at least one of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy and hydroxyl groups is produced asymmetrically by the reaction of 1,3-dibenzyl-cis-4,5-dicarboxy-imidazolidin-2-one or its anhydride with an optically active secondary amine of the formula: ##STR2## wherein R.sup.1 and R.sup.2 are each as defined above and is transformed into the lactone of 1,3-dibenzyl-cis-4-carboxy-5-hydroxymethyl-imidazolidin-2-one, which is a key intermediate in the synthesis of d-biotin.

REFERENCES:
patent: 3700659 (1972-10-01), Gerecke et al.
patent: 3876656 (1975-04-01), Aoki et al.
patent: 4014895 (1977-03-01), Aoki et al.
Ohrui, H., et al., Tetrahedron Letters, No. 32, pp. 2765-2766 (1975).
Confalone, P., et al., Journal of the American Chemical Society, vol. 97, pp. 5936-5938, (1975).
Morrison, J., et al., Asymmetric Organic Reactions, Prentice Hall, New York, 1970, pp. 419-424.
Chemical Abstracts, 83:28227s (1975) [Japan. Kokai 74,127,994, Aoki et al., 12/07/74].
March, J., Advanced Organic Chemistry, McGraw Hill, New York, 1968, pp. 336-337.

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