Stereoselective synthesis of 2-amino-1-hydroxy-3-phenylpropylphosphonic acid

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 24, 1996, Pages 2989-2992

  Zygmunt, Jan ^b   Gancarz, Roman ^c   Lejczak, Barbara ^c   Wieczorek, Piotr ^a   Kafarski, Paweł ^c  

^a UNIVERSITY OF OPOLE   (Poland)

^b UNIVERSITY OF KANSAS   (United States)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 1 HYDROXY 3 PHENYLPROPYLPHOSPHONIC ACID; GLYPHOSATE; HERBICIDE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TOXICITY; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE; PLANT GROWTH;

EID: 0030591870     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(96)00545-8     Document Type: Article

References (17)

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14. 6. General procedure: To the solution of amino alcohol (3; 16 mM) and triethylamine (6.6 ml; 47.7 mM) in DMSO (20 ml) freshly prepared pyridine-sulfur trioxide complex (48 mM) in DMSO (30 ml) was added and the mixture left for 20 min. at room temperature. The reaction mixture was then dissolved in icy-cold water (150 ml) and the product was extracted into ethyl ether (5×50ml). Ethereal solution was then washed succesively with: 10% solution of citric acid (2×10ml), water (3×10ml), saturated sodium hydroxide (10 ml) and water (10 ml). The solution was dried over magnesium sulphate. After removal of drying agent, diethyl phosphite (16 mM) and 3 drops of triethylamine were added and ether was removed under reduced pressure. The resulting oil was left at 24 h at room temperature in 20ml of benzene. Then concentrated hydrochloric acid (100 ml) was added and the mixture was refluxed for 10 h. The volatile components were removed in vacua, the obtained oil dissolved in water (50 ml), decolorized with charcoal and water was removed under reduced pressure. The oily residue was dissolved in methanol (30 ml) and the pure aminophosphonic acid (1) precipitated with propylene oxide.
15. 7. N.m.r. spectra were taken at 250MHz Bruker AMX apparatus.
16. 8. For example: P. Wieczorek, D. Miliszkiewicz, B. Lejczak, M. Soroka, P. Kafarski, Pestic. Sci., 1994, 40, 57.
17. 9. Dixon's Q-test was used to reject the unreasonable results. The means for samples and controls were compared by testing the null hypothesis at the 5% significance level. See: J. C. Miller,. and J. N. Miller, Statistics for Analytical Chemistry. Elllis Harwood Ltd., Chichester, 1984, Chapter 3.