A simple and efficient preparation of (arylphosphinyl)methylphosphonates

Synthetic Communications

Volumn 32, Issue 19, 2002, Pages 2951-2957

  Luke, George P ^a   Shakespeare, William C ^a  

^a NEUROGEN CORPORATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; AROMATIC COMPOUND; DIETHYL(ETHOXYPHOSPHINYL)METHYLPHOSPHONATE; FUNCTIONAL GROUP; HALIDE; METHYLPHOSPHONIC ACID; PALLADIUM; PHOSPHINE DERIVATIVE; PHOSPHINYLMETHYLPHOSPHONATE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

EID: 0036385363     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120012983     Document Type: Article

References (23)

1. (a) Trowbridge, D.B.; Kenyon, G.L. Adenosine 5′-Bis(dihydroxyphosphinylmethyl)phosphinate, the α,β:β,γ-Bismethylene Analog of Adenosine 5′-Triphosphate. J. Am. Chem. Soc. 1970, 92(7), 2181-2182;
2. (b) Shirokova, E.A.; Shipitsin, A.V.; Victorova, L.S.; Dyatkina, N.B.; Goryunova, L.E.; Beabealashvilli, R.Sh.; Hamilton, C.J.; Roberts, S.M.; Krayevsky, A.A. Modified Nucleoside 5′-Triphosphonates as a New Type of Antiviral Agents. Nucleosides Nucleotides 1999, 18(4&5), 1027-1028;
3. (c) Shipitsin, A.V.; Victorova, L.S.; Shirokova, E.A.; Dyatkina, N.B.; Goryunova, L.E.; Beabealashvilli, R.Sh.; Hamilton, C.J.; Roberts, S.M.; Krayevsky, A. New Modified Nucleoside 5′-Triphosphates: Synthesis, Properties Towards DNA Polymerases, Stability in Blood Serum and Antiviral Activity. J. Chem. Soc. Perkin Trans. 1 1999, 1039-1050.
4. (a) McClard, R.W.; Fujita, T.S.; Stremler, K.E.; Poulter, C.D. Novel Phosphonylphosphinyl (P-C-P-C) Analogues of Biochemically Interesting Diphosphates. Syntheses and Properties of P-C-P-C-Analogues of Isopentenyl Diphosphate and Dimethylallyl Diphosphate. J. Am. Chem. Soc. 1987, 109(18), 5544-5545;
5. (b) Biller, S.A.; Forster, C.; Gordon, E.M.; Harrity, T.; Scott, W.A.; Ciosek, Jr., C.P. Isoprenoid (Phosphinylmethyl)phosphonates as Inhibitors of Squalene Synthetase. J. Med. Chem. 1988, 31(10), 1869-1871.
6. Flohr, A.; Aemissegger, A.; Hilvert, D. α-Functionalized Phosphonylphosphinates: Synthesis and Evaluation as Transcarbamoylase Inhibitors. J. Med. Chem. 1999, 42(14), 2633-2640.
7. +-Phosphate Cotransport Across Renal Brush Border Membrane. J. Med. Chem. 1992, 35(26), 4885-4892;
8. +-Phosphate Cotransport Across Renal Brush Border Membrane, by X-ray Crystallographic Analysis of Its (-)-Quinine Salt. J. Med. Chem. 1995, 38(9), 1575-1578.
9. (a) Ebetino, F.H.; Degenhardt, C.R.; Jamieson, L.A.; Burdsall, D.C. Recent Work on the Synthesis of Phosphonate-Containing, Bone-Active Heterocycles. Heterocycles 1990, 30(2), 855-862;
10. (b) McOsker, J.E. Methods for the Treatment of Osteoporosis. WO 92/14474, September 3, 1992;
11. (c) Geddes, A.D.; Boyce, R.W. Methods for the Treatment of Osteoporosis Using Bisphosphonates and Parathyroid Hormone. WO 93/11786, June 24, 1993.
12. (a) Gilmore, W.F.; Park, J.S. Base-Catalyzed Reactions of Phosphonomethylphosphinates, Bis(phosphonomethyl)phosphinates, and Bis(phosphonomethyl)phosphinic Amides with Aldehydes. In Phosphorus Chemistry; ACS Symposium Series 171; American Chemical Society: Washington, DC, 1981; pp 611-614;
13. (b) Prashad, M. Phosphonate vs. Phosphinate Elimination During Olefination of Aldehydes. Tetrahedron Lett. 1993, 34(10), 1585-1588 and references cited therein.
14. Gloyna, D.; Lachman, U.; Henning, H.G. Preparation of Methylene-P Compounds With Different Phosphorous Substituents. J. Prakt. Chem. 1975, 317(5), 840-852.
15. Gobel, R.; Richter, F.; Weichmann, H. Synthesis and Reactivity of Methylene Bridged Diphosphonyl Compounds. Phosphorus, Sulfur Silicon Relat. Elem. 1992, 73(1-4), 67-80.
16. Vu, C.B. Unpublished results.
17. Hirao, T.; Masunaga, T.; Ohshiro, Y.; Agawa, T. A Novel Synthesis of Dialkyl Arenephosphonates. Synthesis 1981, 56-57.
18. Petrakis, K.S.; Nagabhushan, T.L. Palladium-Catalyzed Substitutions of Triflates Derived from Tyrosine-Containing Peptides and Simpler Hydroxyarenes Forming 4-(Diethoxyphosphinyl)phenylalanines and Diethyl Arylphosphonates. J. Am. Chem. Soc. 1987, 109(9), 2831-2833.
19. Xu, Y.; Zhang, J. Palladium-Catalyzed Synthesis of Functionalised Alkyl Alkylarylphosphinates. Synthesis 1984, 778-782.
20. Diethyl (ethoxyphosphinyl)methylphosphonate (2) can readily be prepared in multi-ten-gram quantities in three steps from commercially available materials. Baxter, A.D.; Taylor, R.J.; Collingwood, S.P. Intermediates for Dinucleotide and Oligonucleotide Analogues. US Patent 5,952,478, September 14, 1999; Baillie, A.C.; Wright, B.J.; Wright, K. Pesticidally Active Salts and Compositions Containing Them and Processes for Their Manufacture and Use. EP0009348, April 2, 1980.
21. Diethyl (ethoxyphosphinyl)methylphosphonate (2) can readily be prepared in multi-ten-gram quantities in three steps from commercially available materials. Baxter, A.D.; Taylor, R.J.; Collingwood, S.P. Intermediates for Dinucleotide and Oligonucleotide Analogues. US Patent 5,952,478, September 14, 1999; Baillie, A.C.; Wright, B.J.; Wright, K. Pesticidally Active Salts and Compositions Containing Them and Processes for Their Manufacture and Use. EP0009348, April 2, 1980.
22. 2: C, 39.12; H, 5.30. Found: C, 39.00; H, 5.26.
23. The authors wish to thank Dr. Raji Sundaramoorthi for the preparation of 3i.