13590-71-1Relevant articles and documents
First synthesis of etidronate partial amides starting from PCl3.
Turhanen, Petri A,Niemi, Riku,Peraekylae, Mikael,Jaervinen, Tomi,Vepsaelaeinen, Jouko J
, p. 3223 - 3226 (2003)
Methods for the preparation of mixed tetra-amide esters 1 and 2, the partial amide ester 3, and tri- and P,P-diamides 4 and 5 from monophosphorus spieces 12, 8 and 9, respectively, were developed. Compounds 8 and 9 were obtained from phosphorus trichloride via MeOPCl2, which was treated with 2 eq. and 4 eq. of piperidine, followed by water or acetyl chloride, respectively. Tetrasubstituted amide bisphosphonates 1 and 2 were selectively dealkylated with lithium or silyl halide to achieve target compounds 3-5. Piperidine was found to be a good desilylation reagent. Quantum mechanical calculations illustrate why derivative 2 was produced in low yield. The usefulness of compounds 1, 3 and 4 as prodrugs of etidronate was determined in aqueous buffer and human serum.
Novel routes to aminophosphonic acids: Interaction of dimethyl H-phosphonate with hydroxyalkyl carbamates
Troev,Koseva,Haegele
, p. 119 - 124 (2008)
It was found that the reaction of dimethyl H-phosphonate (1) with 2-hydroxyalkyl-N-2′-hydroxyalkyl carbamates at 135°C includes several chemical reaction steps: (i) chemical transforma-tions of 1-methyl-2- hydroxyethyl-N-2′-hydroxyethyl carbamate (2) and 2-methyl-2-hydroxyethyl- N-2′-hydroxyethyl carbamate (3); (ii) transesterification of dimethyl H-phosphonate with 2 and 3, and with secondary hydroxyl-containing compounds that are formed during the course of the chemical transformation of 2-hydroxyalkyl-N-2′-hydroxyalkyl carbamates; (iii) hydrolysis of 1 and dialkyl H-phosphonates, formed via transesterification of 1 with secondary hydroxyl-containing compounds. The interaction was studied by means of 1H, 13C, 31P NMR, and FAB mass spectroscopy.
Protonation and alkylation of organophosphorus compounds with trifluoromethanesulfonic acid derivatives
Tolstikova,Bel'Skikh,Shainyan
experimental part, p. 474 - 480 (2011/06/23)
Protonation (alkylation) of triphenylphosphine, triethylphosphite, triphenylphosphine oxide, triethylphosphate, hexamethylphosporamide, and dimethylphosphite with trifluoromethanesulfonic acid, its bisimide, and methyl ester was studied and the corresponding 1H, 13C, 19F, 31P NMR spectra were analyzed.
Reconsideration of the base-free batch-wise esterification of phosphorus trichloride with alcohols
Fakhraian,Mirzaei
, p. 401 - 404 (2013/09/05)
Batch-wise esterification of phosphorus trichloride with different alcohols in the absence of base and cleavage of the reaction products by the HCl released in course of the reaction were reinvestigated. The role of the kind of alcohol, mixing order of reagents, temperature, time of reaction, and excursion of gaseous HCl in the proportional composition of the reaction products were studied. Considering the mechanism of esterification and cleavage of the products, the optimized conditions to retain the cleavage process and high-yield production of dialkyl hydrogen phosphonates were determined.
