Sodium Methoxide → 2-(1,1-dimethylethoxycarbonylamino)-N-{2-[3-methoxy-4-(4-chlorophenyl-prop-2-ynyloxy)-phenyl]-ethyl}-3-methylbutyramide

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Reaction Steps

A mixture 2-(1,1-dimethylethoxycarbonylamino)-N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-3-methylbutyramide (4.0 g), toluene-4-sulfonic acid 3-(4-chloro-phenyl)-prop-2-ynyl ester (5.3 g) and 1M sodium methoxide solution in methanol (18 ml) in methanol (100 ml) is heated to reflux for 3 hours . Then the solvent is removed by distillation. Water (300 ml) is added. The mixture is extracted with ethyl acetate (2×200 ml) and washed with brine (100 ml). The organic layers are collected, dried (MgSO4) and evaporated. 2-(1,1-dimethylethoxycarbonylamino)-N-{2-[3-methoxy-4-(4-chlorophenyl-prop-2-ynyloxy)-phenyl]-ethyl}-3-methylbutyramide is obtained which is purified by flash column chromatography on silica gel (ethyl acetate/hexane 1:1) and recrystallisation (ethyl acetate/hexane), m.p. 141-142° C.

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