Process for preparing macrolide derivatives

Details Process for preparing macrolide derivatives Process for preparing macrolide derivatives

1986-03-31

1990-05-01

Lilling, Herbert J.

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

Organic compounds

Carbohydrates or derivatives

536124, C07M 100

Patent

active

049219472

ABSTRACT:
This invention provides an improvement in the process for preparing C-20-amino-substituted derivatives of the macrolide antibiotics of the tylosin type by reductively aminating the C-20 aldehyde group in the parent antibiotic. The improvement comprises using formic acid as the reducing agent. The new process is less expensive and more amenable to scale-up than previously used processes, but is still selective.

REFERENCES:
patent: 4440759 (1984-04-01), Omura et al.
patent: 4443436 (1984-04-01), Kirst et al.
patent: 4454314 (1984-06-01), Nagel
patent: 4468511 (1984-08-01), Kirst et al.
patent: 4517359 (1985-05-01), Kobrehel et al.
Matsubara et al., "Chemical Modificatoins of Tylosin: Synthesis of Amino Derivatives of C-20 Position of Tylosin and Demycarosyltylosin," J. Antibiotics 36 (12), 1713-1721 (1983).
Omura et al., "Novel Dimeric Derivatives of Leucomycins and Tylosin, Sixteen-Membered Macrolides," J. Med. Chem. 25, 271-275 (1982).
DeBenneville et al., "The Behavior of Aliphatic Aldehydes in the Leuckart-Wallach Reaction," J. Amer. Chem. Soc. 72, 3073-3075 (1950).
Bach, "Preparation of Tertiary N,N-Dimethylamines by the Leuckart Reaction," J. Org. Chem. 33 (4), 1647-1649 (1968).
Davis et al., "Steroid Amines. Part V. 20-Pyrrolidin-1-ylpregnane Derivatives," J. Chem. Soc. Perkin I 1972, 1420-1424.
Debono et al., Chem. Abstr. 101(13):111343n, Abstract of European Patent Appln. EP103465A1, Mar. 21, 1984.
Debono et al., Chem. Abstr. 102(13):113885k, Abstract of U.K. Patent Appln. GB2,135,670A1, Sep. 5, 1984.
"Weygand/Hilgetag Preparative Organic Chemistry", G. Hilgetag and A, Martini, Eds, John Wiley and Sons, New York, 1972, pp. 524-527.

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