Preparation of dehydropeptides

Details Preparation of dehydropeptides Preparation of dehydropeptides

1979-10-01

1981-04-14

Phillips, Delbert R.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

C07C10352

Patent

active

042618843

ABSTRACT:
A preparation of azlactones represented by the formula ##STR1## wherein R is a substituted or unsubstituted alkyl, aryl or nitrogen containing heterocyclic group, and R.sup.1 is an N-blocked amino acid residue or peptide chain, and stereoisomers thereof, by oxidizing the corresponding saturated azlactone with a benzoquinone oxidizing agent in the presence of a base is disclosed. The unsaturated azlactones, some of which are novel, can be converted to dehydro peptides, which are useful as intermediates for preparing novel biologically active compounds, or themselves have biological activity.

REFERENCES:
Rich, et al., J.C.S., 1974, 897-898.
Riordan, et al., Tetrahedron Letter, No. 16, 1976, 1247-1250.
Bodanszky et al., Chem. Abstr. 72 1970, 83007t.
Weiner et al., J.A.C.S. 88, 1966, 3851-3859.
Doherty et al., J. Biol. Chem. 147, 1943 617-637.
Benoiton et al., J. Chem. Soc. 1964, 824-836.
Patchornik et al., J.A.C.S. 86, 1860-1861 1964.

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