Ammonium Chloride → HCID 67029513, compound

Participants

Reaction Conditions

Reaction Steps

{4-[2-(tert-Butoxycarbonyl)hydrazinocarbonylmethyl]benzyl}(triphenyl)phosphonium chloride (2.97 g, 5.29 mmol) was suspended in anhydrous tetrahydrofuran (8 ml), and cooled to −78° C. n-Butyllithium (1.6M-hexane solution, 3.3 ml, 5.3 mmol) was added dropwise, and the mixture was stirred at −78° C. for 15 mins and at 0° C. for 2 hrs. A solution of N-(5-formylthiophen-2-yl)acetamide (280 mg, 1.65 mmol) in anhydrous tetrahydrofuran (2 ml) was added dropwise, and the mixture was warmed to room temperature. After stirring at room temperature overnight, saturated aqueous ammonium chloride solution was added. The mixture was extracted with dichloromethane and the combined organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (dichloromethane:methanol=97:3→80:20) to give tert-butyl 2-({4-[2-(5-acetylaminothiophen-2-yl)vinyl]phenyl}acetyl)hydrazinecarboxylate (192 mg, yield 28%, E/Z mixture) as a yellow solid.

Provenance & Evidence