Hydrochloric Acid → (E)-(R)-4-tert-butoxycarbonylamino-6-(4-heptyloxy-phenyl)-4-methyl-hex-2-enoic acid

Participants

Reaction Steps

To a stirred solution of (E)-(R)-4-tert-butoxycarbonylamino-6-(4-heptyloxy-phenyl)-4-methyl-hex-2-enoic acid ethyl ester (56 mg, 0.12 mMol) in methanol (0.5 ml), THF (0.5 ml) and water (0.5 ml) is added lithium hydroxide (14 mg, 0.61 mMol). The mixture is stirred at RT for 3.5 hours. The reaction mixture is then poured onto a biphasic mixture of AcOEt and HCl (aqueous, 1 M). The aqueous phase is extracted twice with AcOEt. The combined organic layers are washed with a small amount of NaHCO3 (saturated aqueous solution), dried (Na2SO4) and concentrated under reduced pressure to give the title compound. The crude product is sufficiently pure to be used in the next stage without further purification.

Provenance & Evidence