methyl (S)-2-amino-3-(4-but-2-ynyloxy-phenyl)-propionate → 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

Participants

Reaction Conditions

Reaction Steps

tert-Butyl (E)-(2S,3S)-2-hydroxy-3-((S)-4-isopropyl-5,5-diphenyl-2-thioxo-oxazolidine-3-carbonyl)-2-propyl-10-(2-trimethylsilanyl-ethoxycarbonylamino)-dec-4-enoate (582 mg, 0.759 mmol) and methyl (S)-2-amino-3-(4-but-2-ynyloxy-phenyl)-propionate (376 mg, 1.52 mmol) were dissolved in dichloromethane (10 mL), and dichloromethane was then distilled off under reduced pressure. The obtained mixture was warmed at 40° C. for 41 hours. The reaction mixture was purified on Biotage (silica gel, n-hexane/ethyl acetate) to obtain 443 mg (0.0618 mmol, 81% yield) of 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.

Provenance & Evidence