Development of a Multikilogram Synthesis of a Chiral Epoxide Precursor to a CCR1 Antagonist. Use of in Situ Monitoring for Informed Optimisation via Fragile Intermediates
Organic Process Research & Development2009Vol. 14(1), pp. 72–84
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Debra Ainge, J.E.M. Booker, Nicholas I. Pedge, R. S. Sinclair, Chris J. Sleigh, Marijan Štefinović, Luis-Manuel Vaz, Edward L. Way
Abstract
The optimisation and scale up of a manufacturing route to a key intermediate, acetic acid 4-acetylamino-3-(2-methyl-oxiranylmethoxy)phenyl ester (2), utilising a SNAr coupling, the hydrogenation of a nitro moiety and the conversion of a chiral acetonide into a chiral epoxide is described along with other routes to access intermediate 2 including the chemoselective reduction of a nitro moiety in the presence of an epoxide.
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