反应详情

温度

5 °C

(S)-N-Methylsulfonyl)-2-oxo-3-amino-1-azetidinecarboxamide, hydrochloride salt (189 mg; see example 6) was suspended in 8 ml of dry acetonitrile and 0.54 ml of triethylamine, and stirred at room temperature under nitrogen until solution occurred (about 15 minutes). The solution was cooled to 0°to 5° C., and then phenyl acetylchloride (153 μl) was added. The reaction was stirred at room temperature for 3 hours and then poured into 10 ml of 0.5 M pH 5.5 monobasic potassium phosphate buffer. The pH was adjusted to 7 (dilute potassium hydroxide) and the solution was extracted twice with ethyl acetate. The aqueous layer was covered with fresh ethyl acetate, and the pH was adjusted to 2 (3N hydrochloric acid). Repeated extraction with ethyl acetate gave an acidic ethyl acetate extract, which was dried (sodium sulfate) and evaporated to a residue (196 mg). Chromatography of this material on 20 g of SilicAR CC-4 using ethyl acetate/dichloromethane (1:1) provides 96 mg of crystalline product after removal of solvent. Recrystallization from ethyl acetate/dichloromethane provides an analytical sample having a melting point 168°-170° C., dec.

1. custom(about 15 minutes)
2. extractionthe solution was extracted twice with ethyl acetate
3. extractionextraction with ethyl acetate
4. customgave an acidic ethyl acetate
5. extractionextract
6. dry with materialwhich was dried (sodium sulfate)
7. customevaporated to a residue (196 mg)