4-Benzyl 1,4-di-tert-butyl (1S)-5-[5-(benzyloxy)pyridin-2-yl]-1-[(tert-butoxycarbonyl)amino]pentane-1,4,4-tricarboxylate → (5S)-6-tert-Butoxy-2-(tert-butoxycarbonyl)-5-[(tert-butoxycarbonyl)amino]-2-[(5-hydroxypyridin-2-yl)methyl]-6-oxohexanoic acid

Participants

Reaction Steps

To a solution of 310 mg of 4-benzyl 1,4-di-tert-butyl (1S)-5-[5-(benzyloxy)pyridin-2-yl]-1-[(tert-butoxycarbonyl)amino]pentane-1,4,4-tricarboxylate (0.44 mmol) in methanol (10 mL) was added a 10% palladium on carbon hydrogenation catalyst (15 mg) at room temperature. The suspension was stirred for 3 h at room temperature under an atmosphere of hydrogen. The catalyst was removed by filtration and all volatiles were removed in vacuo. The crude product (234 mg, quantitative yield) was used in the next step without further purification.

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