Taxanes prepared by beta-lactams and ammonium alkoxides

Details Taxanes prepared by beta-lactams and ammonium alkoxides Taxanes prepared by beta-lactams and ammonium alkoxides

C - Chemistry, Metallurgy

07

D

C07D 305/14 (2006.01) C07C 227/22 (2006.01) C07C 231/00 (2006.01) C07C 231/12 (2006.01) C07C 233/87 (2006.01) C07D 405/12 (2006.01) C07D 407/00 (2006.01) C07D 407/12 (2006.01) C07D 409/00 (2006.01) C07D 409/12 (2006.01) C07F 7/08 (2006.01) C07F 7/18 (2006.01)

Patent

CA 2158458

A process for preparing N-acyl, N-sulfonyl and N-phosphoryl substituted isoserine esters in which an ammonium alkoxide is reacted with a .beta.-lactam. The process is for the preparation of a substituted isoserine ester having the formula (see formula one) comprising reacting a .beta.-lactam with an alkoxide, the .beta.-lactam having the formula: (see formula two) and the alkoxide having the formula MOCE1E2E3 wherein X1 is -OX6, -SX7, or -NX8X9; X2 is hydrogen, alkyl, alkenyl, alkynyl, aryl, or heteroaryl; X3 and X4 are independently hydrogen, alkyl, alkenyl, alkynyl, aryl, substituted aryl, heteroaryl, acyl or hetero-substituted alkyl, alkenyl, alkynyl, aryl or heteroaryl, provided, however, that X3 and X4 are not both aryl; X5 is -COX10, -COOX10, -COSX10, -CONX8X10, or -SO2X11; X6 is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, hydroxy protecting group, or a functional group which increases the water solubility of the taxane derivative; X7 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, or sulfhydryl protecting group; X8 is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, or heterosubstituted alkyl, alkenyl, alkynyl, aryl or heteroaryl; X9 is an amino protecting group; X10 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, or heterosubstituted alkyl, alkenyl, alkynyl, aryl, substituted aryl or heteroaryl; X11 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, -OX10, or -NX8X14; X14 is hydrogen, alkyl, alkenyl, alkynyl, aryl, or heteroaryl; E1, E2 and E3 are independently hydrogen, hydrocarbon or cyclic, provided, at least one of E1, E2 and E3 is other than hydrogen; and M is an ammonium- containing substituent.

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