Process for producing phosphonomycin

Details Process for producing phosphonomycin Process for producing phosphonomycin

1978-06-16

1980-09-16

Milestone, Norma S.

Chemistry of carbon compounds

Dipeptides, e.g., aspartame, anserine, carnosine, etc.

26034831, 26034842, C07F 940

Patent

active

042229707

ABSTRACT:
A novel synthesis of the antibiotic phosphonomycin provided which avoids formation of butylphosphochloridite and instead obtains the intermediate butyl-propinyl-phosphite by the mixed anhydrides method. Simplified reaction apparatus is used. Very high yields of a further intermediate, di-t-butylpropadienylphosphate are obtained using the mixed anhydrides process starting with dibutylphosphite. The synthesis of phosphomycin is carried further by hydrogenation of the di-t-butylpropadienylphosphonate using hydrazine hydrate and Ni-Raney with excellent yields to give the second intermediate di-t-butyl-cis-1,2-propenylphosphonate which is in turn converted to the desired phosphomycin by converting to the free phosphonic acid e.g., by reflux with strong acid to remove the t-butoxy groups, followed by epoxidation of the resultant phosphonic acid with hydrogen peroxide and sodium tungstate to yield cis-1,2-epoxypropylphosphonic acid. Optical resolution is then carried out by selective crystallization with (+)-.alpha.-phenylethylamine and recrystallization.

REFERENCES:
patent: 3188309 (1965-06-01), Mukalyama et al.
patent: 3597451 (1971-08-01), Firestone
patent: 3849482 (1974-11-01), Christensen et al.
E. J. Glamkowski et al., J. Org. Chem., vol. 35, No. 10 (1970) 3510-3512.
Chemical Abstracts, vol. 58 (1963) 1322b.

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