methyl (S)-2-amino-3-(4-butoxy-phenyl)-propionate → tert-butyl (E)-(2S,3S)-3-[(S)-2-(4-butoxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-12,12-difluoro-2-hydroxy-2-(2-methoxy-ethyl)-nonadec-4-enoate

Participants

Reaction Conditions

Reaction Steps

tert-Butyl (E)-(2S,3S)-12,12-difluoro-2-hydroxy-3-((S)-4-isopropyl-2-oxo-5,5-diphenyl-thiazolidine-3-carbonyl)-2-(2-methoxy-ethyl)-nonadec-4-enoate (No. 5552816; 17.0 mg, 0.0216 mmol) and methyl (S)-2-amino-3-(4-butoxy-phenyl)-propionate (8.2 mg, 0.0324 mmol) were dissolved in dichloromethane and the solvent was distilled off. The resulting mixture was stirred at 50° C. for 2.5 days, cooled to room temperature, and subsequently the residue was purified by preparative TLC (33% ethyl acetate/n-hexane, Rf=0.6) to obtain tert-butyl (E)-(2S,3S)-3-[(S)-2-(4-butoxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-12,12-difluoro-2-hydroxy-2-(2-methoxy-ethyl)-nonadec-4-enoate (No. 5552820; 13.9 mg, 87% yield).

Provenance & Evidence