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-11-[2-(4-phenyl-butyl)-[1,3]dioxolan-2-yl]-2-propyl-undec-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)-11-[2-(4-phenyl-butyl)-[1,3]dioxolan-2-yl]-2-propyl-undec-4-enoate (124 mg, 0.150 mmol) and methyl (S)-2-amino-3-(4-but-2-ynyloxy-phenyl)-propionate (70.0 mg, 0.283 mmol) were dissolved in dichloromethane (3.0 mL). Dichloromethane was distilled off under reduced pressure. The residue was then stirred at an outer temperature of 50° C. for 24 hours. The reaction mixture was purified on Biotage (silica gel, n-hexane/ethyl acetate) to obtain 72.0 mg (0.0928 mmol, 62% yield, purity 78%) of tert-butyl (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-hydroxy-11-[2-(4-phenyl-butyl)-[1,3]dioxolan-2-yl]-2-propyl-undec-4-enoate (ESI (LC/MS positive mode) m/z 776 (M+H); Rt 2.47 min.).

Provenance & Evidence