tert-butyl (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-hydroxy-2-propyl-10-(2-trimethylsilanyl-ethoxycarbonylamino)-dec-4-enoate → tert-butyl (E)-(2S,3S)-10-amino-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-hydroxy-2-propyl-dec-4-enoate

Participants

Reaction Steps

tert-Butyl (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-hydroxy-2-propyl-10-(2-trimethylsilanyl-ethoxycarbonylamino)-dec-4-enoate (298 mg, 0.415 mmol) was dissolved in nitromethane (1.5 mL), and zinc chloride (235 mg, 1.72 mmol) was then added at room temperature. The mixture was stirred for 4 hours, and then purified by preparative HPLC to obtain 192 mg (0.335 mmol, 81% yield) of tert-butyl (E)-(2S,3S)-10-amino-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-hydroxy-2-propyl-dec-4-enoate.

Provenance & Evidence