Sodium Hydroxide → (4R,5E)-4-tert-butoxycarbonylamino-7-oxo-8-(3,5-dimethylphenyl)oct-5-enoic acid ethyl ester

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Reaction Steps

Under atmosphere of argon, a suspension of 60% sodium hydride (50 mg) was added by a solution of dimethyl (2-oxo-3-(3,5-dimethylphenyl)propyl)phosphonate (373 mg) in tetrahydrofuran (5 mL) at the temperature of 0° C. The mixture was stirred for an hour and then a solution of ethyl (4R)-4-(tert-butoxycarbonylamino)-4-formylbutanoate (298 mg) in tetrahydrofuran (5 mL) was added to the mixture. The mixture was stirred for an hour. To the mixture, metyl tert-butyl ether and water were added, and then 1N a solution of sodium hydroxide was added. The organic layer was washed with saturated brine, dried over an anhydrous magnesium sulfate, concentrated and was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1) to give the title compound (300 mg) having the following physical data.

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