Synthesis of 4-[4′-bis(2″-chloroethyl)aminophenyl] -3-(difluoromethyl) butanoic acid [3-(difluoromethyl)chlorambucil]

Add time:07/12/2019    Source:sciencedirect.com

Benzyl chlorodifluoromethyl ketone, ethyl bromoacetate and zinc afforded ethyl 3-(chlorodifluoromethyl)-3-hydroxy-4-phenylbutanoate in a Reformatsky-type reaction. By successive stages of dehydration to a mixture of but-2-and -3-enoates; simultaneous hydrogenation of the double bond and replacement of Cl by H nitration; and conversion of the nitro-group to amino; this hydroxy-ester was converted into ethyl 4-(4′-aminophenyl)-3-(difluoromethyl)butanoate. Treatment of this with oxirane gave the bis(2″-hydroxyethyl)-amino-derivative, from which the bis(chloroethyl)-analogue was made using Ph3P/CCl4. The target chlorambucil, bearing a difluoromethyl group at position 3, was then obtained after hydrolysis of the ester.

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