Triphenylphosphine → HCID 69692767, compound

Participants

Reaction Steps

A mixture of 0.22 g (0.41 mmol), (S)-3-[4-(4-dimethylamino-butanoylamino)-2-hydroxy-benzensulfonylamino]-4,4-diethoxy-butyric acid tert-butyl ester, 0.079 g (0.41 mmol), 2-quinolin-5-yl-ethanol, 0.14 g (0.62 mmol) triphenylphosphine, and anhydrous methylene chloride (5 mL) was stirred at room temperature. Diethyl azodicarboxylate 0.1 mL (0.62 mmol) was added dropwise and the resulting orange solution was stirred at room temperature for 24 h. TLC analysis indicated complete reaction. The reaction mixture was concentrated in vacuo to give a deep yellow oil. The product was purified over silica eluting with 10% (8:1 EtOH/NH4OH): 90% methylene chloride to yield 0.115 g (0.17 mmol, 41%) of (S)-3-[4-(4-dimethylamino-butanoylamino)-2-(2-quinolin-5-yl-ethoxy) benzensulfonylamino]-4,4-diethoxy-butyric acid tert-butyl ester as a yellow oil. MS (APCI) m/z 685.5 (M−1).

Provenance & Evidence