Réaction #42507

Équation de réaction

diisopropylethylamine

3-(Allylthio)benzoic acid

(2R,3R)-3-amino-4-(3,5-difluorophenyl)-1-{[1-(3-ethylphenyl)cyclopropyl]amino}butan-2-ol

HATU

→

desired compound

Rendement 176.8%

3-(allylthio)-N-((1S,2R)-1-(3,5-difluorobenzyl)-3-{[1-(3-ethylphenyl)cyclopropyl]amino}-2-hydroxypropyl)benzamide

Rendement 176.8%

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   ConcentrationUpon completion, the reaction mixture was concentrated
2. 2
   Autrechromatographed (SiO2, 2:1 to 1:1 Hexanes: EtOAc)

Mode opératoire

3-(Allylthio)benzoic acid (717 mg, 3.69 mmol), (2R,3R)-3-amino-4-(3,5-difluorophenyl)-1-{[1-(3-ethylphenyl)cyclopropyl]amino}butan-2-ol (247mg, 0.685 mmol), and HATU (Aldrich, 2.1 g, 5.54 mmol) were dissolved in dichloromethane (35 mL), at ambient temperature, and treated with diisopropylethylamine (1.6 mL, 9.225 mmol). Upon completion, the reaction mixture was concentrated and chromatographed (SiO2, 2:1 to 1:1 Hexanes: EtOAc) to give the desired compound (650 mg). (LRMS (M+H) m/z=537.8)

Source