Method for preparing a phosphonic acid ester

Organic compounds -- part of the class 532-570 series – Organic compounds – Phosphorus esters

Patent

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

558136, 558137, 558161, C07F 940, C07F 938

Patent

active

052102629

ABSTRACT:
A method is provided for preparing a phosphonic acid ester having the structure ##STR1## wherein R.sup.1 is farnesyl or a derivative or analog thereof, and R.sup.2 is lower alkyl, by treating a farnesyl halide R.sup.1 Hal(Hal=Cl,Br,I) with an alkoxide of the structure ##STR2## wherein M is an alkali metal and R.sup.2c is lower alkyl. The resulting phosphonic acid ester is an intermediate in preparing a squalene synthetase inhibitor which is used for inhibiting cholesterol biosynthesis.

REFERENCES:
patent: 3733379 (1973-05-01), Szabo
patent: 4014959 (1977-03-01), Crutchfield et al.
Bronson, J. J. et al., "Synthesis and Antiviral Activity of the Nucleotide Analogue (S)-1-[3-Hydroxy-2-(phosphonylmethoxy)-propyl]cystosine," J. Med. Chem. 1989, 32, 1457-1463.
Wilson, J. R. H. "Synthesis of Diethyl Alkoxymethlphosphonates via Lewis Acid Promoted Regiospecific Cleavage of Alkoxy-4-Chlorophenoxymethanes," J. Chem. Soc. Perkin Trans. I, 1986.
Chem. Abst. 92:186461Z (1980), p. 677, abstract of Petrov, K. A. et al., "Alkoxymethylation of dialkyl, ethylene, and diphenyl chlorophosphites with dialkyl formals".
Arbusov, A. I., Akad. SSSR, Otd. chim. 1959, 35, 38; engl. Ausg. S. 31, 33, 34 (Beilstein Handbuch, 4, Aufl., 4, Erg-Werk, Bd. I/5).
Kiyoshi et al., Chemical Abstracts, vol. 66, No. 38014 (1967).
Aldrich Catalog, p. 1087 (1990).
The Chemist's Companion, by A. J. Gordon and R. A. Ford, pp. 67-69 (1972).
Brown, J. Am. Chem. Soc., 39, p. 3913 (1974).
Pudovik et al., Chemical Abstracts, vol. 69, No. 27492 (1968).
Zaripov et al., Chemical Abstracts, vol. 79, No. 78894 (1973).
Fieser and Fieser's Reagents for Organic Synthesis, vol. 10, p. 324 (1982).
Stork et al., J. Am. Chem. Soc., 101, p. 7107 (1979).
Pudovik et al., Zhurnal Obschei Khimii (English Transl.) p. 678 (1968).
"Mechanism and Structure in Organic Chemistry" by Edwin S. Gould, pp. 286-291, (1959).
"Silicon in Organic Synthesis" by Ernest W. Colvin, pp. 321-323 (1981).

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Method for preparing a phosphonic acid ester does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Method for preparing a phosphonic acid ester, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Method for preparing a phosphonic acid ester will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-1351608

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.