(5S)-6-tert-Butoxy-2-(tert-butoxycarbonyl)-5-[(tert-butoxycarbonyl)amino]-2-[(5-hydroxypyridin-2-yl)methyl]-6-oxohexanoic acid → Di-tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-[(5-hydroxypyridin-2-yl)methyl]hexanedioate

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Reaction Steps

A solution of 220 mg of (5S)-6-tert-butoxy-2-(tert-butoxycarbonyl)-5-[(tert-butoxycarbonyl)amino]-2-[(5-hydroxypyridin-2-yl)methyl]-6-oxohexanoic acid (0.42 mmol) and 100 mg 4-N,N-dimethylaminopyridine (0.84 mmol) in 1,4-dioxan (10 mL) was heated under reflux for 2 hours. The mixture was evaporated and the residue was purified by column preparative HPLC (method C) to give two batches (107+49 mg; 78% combined yield) of the target compound.

Provenance & Evidence