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

Add time:07/11/2019    Source:sciencedirect.com

Benzyl trifluoromethyl ketone and ethyl bromoacetate afforded ethyl 3-hydroxy-4-pheny1-3-(trifluoromethyl)butanoate in a Reformatskytype reaction. This hydroxy ester, by successive stages of dehydration to a but-2-enoate, hydrogenation of the double bond, nitration, and conversion of the nitro group to amino, was converted into ethyl 4-(4′-aminophenyl)-3-(trifluoromethyl)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 trifluoromethyl group was then obtained after hydrolysis of the ester. With DAST, the hydroxy ester afforded the same but-2-enoate as that from the dehydration stage.

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