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Diethyl phosphorocyanidate amides

Diethyl phosphorocyanidate continues to be exploited for the purposes of conventional organic synthesis. Reported applications of the compound include a new conversion of carboxylic acids into esters or amides and also a ring-expansion reaction of 1,3-thiazoles in the penicillin series. Diphenyl phosphorazidate has been employed in a modified Curtius reaction/ in peptide synthesis, and for... [Pg.118]

Shioiri, T., Yokoyama, Y, Kasai, Y, andYamada. S.. Phosphorus in organic synthesis. Part 11. Amino acids and peptides. Part 21. Reaction of diethyl phosphorocyanidate (DEPC) with carboxylic acids. A new synthesis of carboxylic esters and amides. Tetrahedron. 32. 2211. 1976. [Pg.292]

In more recent work involving a series of alkyl, aralkyl and arylamides of MTX and AMT [316], MeAPA was condensed with a-benzyl L-glutamic acid y-3,4-methylenedioxyanilide by the diethyl phosphorocyanidate coupling procedure to obtain the ester amide (VIII. 195). The benzyl ester group in (VIII.195) was then removed with NaOH to form (VIII.196) in 64% overall yield. Further reaction of (VIII.196) with boron tris(trifluoroacetate) in tri-fluoroacetic acid at 0 °C for 15 min afforded MTX y-(3,4-dihydroxyanilide) ((VIII.197) 79% yield). AMT y-amides (VIII.198)-(VIII.205) were prepared via the blocked intermediates (VIII.206)-(VIII.213), which were generated from FmAPA by the modified mixed anhydride route (four activation cycles ... [Pg.203]


See other pages where Diethyl phosphorocyanidate amides is mentioned: [Pg.257]    [Pg.260]    [Pg.257]    [Pg.15]    [Pg.18]    [Pg.703]    [Pg.163]    [Pg.202]    [Pg.260]   
See also in sourсe #XX -- [ Pg.502 , Pg.503 , Pg.504 , Pg.505 , Pg.506 , Pg.507 , Pg.508 , Pg.509 , Pg.510 , Pg.511 , Pg.512 , Pg.513 , Pg.514 ]




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Diethyl phosphorocyanidate

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