Hydrochloric Acid → (2R,4S,5S)-5-amino-4-hydroxy-2-methyl-6-phenylhexanoic acid (3,3-dimethylbutyl)-amide

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Reaction Steps

[(1S,2S,4R)-1-Benzyl-4-(3,3-dimethylbutylcarbamoyl)-2-hydroxypentyl]-carbamic acid t-butyl ester (D1) (264 mg, 0.63 mmol) was treated with 4M HCl in dioxane (5 ml) and the resulting solution was stirred at room temperature for 1 h. It was then evaporated to dryness and the residue was partitioned between satd. aq. sodium carbonate and ethyl acetate. The aqueous layer was separated and extracted with further ethyl acetate. The combined organic extracts were washed with brine, dried over MgSO4, filtered and evaporated to afford product (179 mg, 89%).

Provenance & Evidence