Sodium Chlorite → 3-(1-Ethoxycarbonyl-1-methyl-ethoxy)-5-methoxy-benzoic acid

Participants

Reaction Steps

In analogy to the procedure described in example 50k), 2-[3-methoxy-5-(piperidin-4-ylcarbamoyl)-phenoxy]-2-methyl-propionic acid ethyl ester [prepared by i) oxidation of 2-(3-formyl-5-methoxy-phenoxy)-2-methyl-propionic acid ethyl ester with sodium chlorite in analogy to example 60c) to give 3-(1-ethoxycarbonyl-1-methyl-ethoxy)-5-methoxy-benzoic acid; ii) subsequent condensation with 4-amino-piperidine-carboxylic acid tert-butyl ester, using acid activation with 2-chloro-4,6-dimethoxy-1,3,5-triazine in analogy to the procedure described in example 50 h) followed by Boc cleavage with TFA in analogy to the procedure described in example 50i)] was reacted with 3,5-diethoxy-4-fluoro-benzaldehyde (example 50 g), sodium cyanoborohydride, N-ethyl-diisopropylamine and acetic acid in ethanol at 50° C. to yield the title compound as colorless foam. MS: 561.6 (MH+).

Provenance & Evidence