Pyridine → N-{2-[(3S)-4-hydroxy-3-{(3-methylbutyl)[(4-nitrophenyl)sulfonyl]amino}butyl]phenyl}-Nalpha-(methoxycarbonyl)-beta-phenyl-L-phenylalaninamide

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Reaction Steps

A solution of N-{2-[(3S)-4-{[tert-butyl(diphenyl)silyl]oxy}-3-{(3-methylbutyl)[(4-nitrophenyl)sulfonyl]amino}butyl]phenyl}-Nα-(methoxycarbonyl)-β-phenyl-L-phenyl alaninamide (10, 141.3 mg, 0.148 mmol) in THF (1.5 ml) stirred at 0° C. in a plastic vial, was treated with a 70% solution of HF in pyridine (1.5 mL, 5.8 mmol), the plastic bottle was capped and the final mixture stirred at room temperature for 4 h. Diluted with EtOAc, washed with water followed by saturated NaHCO3, dried over MgSO4, filtered and concentrated. Purification made by passage through a chromatographic cartridge of silicagel (12 g) eluted with 20% to 60% EtOAc in hexane to give 74 g (69% yield) of title compound as white foam. MS: m/z=717.3 (MH+).

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