Diethyl phosphoryl cyanide

DEPC, diethyl phosphorocyanidate, diethyl phosphoryl cyanide, diethyl cyanophosphonate [2942-58-7]... 

Diethyl phosphoryl cyanide or diethyl cyanophosphonate (3) activates carboxylic acid (1) and serves as a coupling agent with amine (2) to provide amide or peptide (4).1-3... 

Diphenyl phosphoryl azide in dimethylformamide followed by triethylamine added at or below 0° to a soln. of N-carbobenzoxy-L-leucyl-L-leucine and L-valyl-L-phenylalanine methyl ester hydrochloride in the same solvent, stirred several hrs. at the above temp, and overnight at room temp. -> product. Y 87%. - Practically no racemization occurred. F. e., also direct prepn. of urethans from carboxylic acids (cf. Synth. Meth. 17, 393) by a simplified Curtius degradation, s. T. Shioiri, K. Ninomiya, and S. Yamada, Am. Soc. 94, 6203 (1972) Tetrah. Let. 1973, 2343 synthesis of N-subst. carboxylic acid amides and peptides with diethyl phosphoryl cyanide s. Tetrah. Let. 1973, 1595 coupling reagents in peptide synthesis, review, s. Y. S. Klausner and M. Bodansky, Synthesis 1972, 453 review of peptide synthesis s. J. Meienhofer, Chem. Technol. 3, 242 (1973). 

Diethyl phosphoryl cyanide triethylamine N-Subst. carboxylic acid amides from carboxylic acids Peptides... 

Diethyl cyanophosphonate is also known as diethylphosphoryl cyanide, diethoxy-phosphoryl cyanide, diethylphosphorocyanidate, diethyl cyanophosphate, and DEPC.13 It can be readily prepared from triethyl phosphite and cyanogen bromide.2 It is very toxic and corrosive and it must be handled in a fame hood. The reagent is moisture sensitive and should be stored under nitrogen in a refrigerator. 

Phosphoryl chloride [10025-87-3], 4 Phthalamic acid, A V-diethyl-, methyl ester [2659344-2],63 Piperidine [110-894], 86, 118 acetate [4540-334], 118 Piperidine, 1 chloro- [2156-71-0], 118 Potassium cyanide [151-50-8], 20... 

Diethyl cyanophosphonate converts quinoline and isoqninoline iV-oxides into the 1- and 2-cyano-heterocycles in high yields in a process which must have 0-phosphorylation as a first step, and in which the elimination of diethylphosphate may proceed via a cyclic transition state trimethylsilyl cyanide and diazabicyclonndecene effect the same transformation. A chloroformate and an alcohol convert the iV-oxides into ethers, as illustrated below for isoquinoline iV-oxide, a chloroformate and a Grignard reagent prodnce 2-snbstitnted quinolines, and a chloroformate then an isonitrile produce 2-carbamoyl-... 

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