Process for preparing alpha-fluorinated alkanediphosphonates

Chemistry of carbon compounds – Dipeptides – e.g. – aspartame – anserine – carnosine – etc.

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260932, 2605024P, C07F 940, C07F 938

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active

044787634

ABSTRACT:
A method for the production of alpha-fluorinated methane diphosphonates consists of the reaction of diphosphonate esters with a strong base, preferably potassium t-butoxide, and perchloryl fluoride to produce alpha-mono and alpha,alpha-difluorinated derivatives which can be converted to the corresponding acids by mild hydrolysis. The synthesis of unsymmetrical alpha-fluorinated methanediphosphonate esters followed by selective hydrolysis produces unsymmetrical diesters of diphosphonic acids.

REFERENCES:
patent: 4330486 (1982-05-01), Burton et al.
McKenna et al., "J. Org. Chem.", vol. 46, pp. 4573-4576, 10/27/1981.
Burton, et al., "J. Fluorine Chem.", vol. 20, pp. 617-626, (1982).
Kosolapoff et al., "Org. Phosphorus Cpds.", vol. 7, p. 181 (1977).
Abstracts Relating to British Patent No.1,026,366; issued Apr. 20, 1966.
Burton, et al., "Preparation of F-Methylene Bis Phosphonates", Journal of Fluorine Chemistry, 15 (1980) pp. 263-266.
Blackburn, et al., "Monofluoro- and Difluoro-methylenebisphosphonic Acids: Isopolar Analogues of Pyrophosphoric Acid", J.C.S. Chem. Comm., 1981, pp. 930-932.

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