Water → Tert-butyl 1-((4-(4-(3-aminopropoxy)benzoyl)phenyl)amino)-3,6,9,12-tetraoxapentadecan-15-oate

Participants

Reaction Steps

Triphenylphosphine (2.62 g, 10.0 mmol) was added to a solution of tert-butyl 1-((4-(4-(3-azidopropoxy)benzoyl)phenyl)amino)-3,6,9,12-tetraoxapentadecan-15-oate (5.0 g 8.32 mmol) in Ether:THF (1:1, 50 mL) at 0° C. followed by of water (500 mg, 27.8 mmol). The reaction was stirred at r.t. overnight. Upon completion, the reaction was concentrated and purified by silica gel chromatography (EtOAc to EtOAc:MeOH gradient with 1% TEA) to provide 3.24 g (5.63 mmo 68.7% yield) of tert-butyl 1-((4-(4-(3-aminopropoxy)benzoyl)phenyl)amino)-3,6,9,12-tetraoxapentadecan-15-oate as yellow oil.

Provenance & Evidence