تفاعل #47671
ord-c340630b5e7a4d41953dd76d267699a5
معادلة التفاعل
المتفاعلات
الكواشف
المذيبات
ظروف التفاعل
المعالجة
- 1درجة الحرارةThe reaction mixture was then cooled to room temperature
- 2ترشيحThe mixture was then filtered
- 3غسيلThe filtrate was washed successively with aqueous saturated ammonium chloride, water, and brine
- 4تجفيفdried over sodium sulfate
- 5ترشيحfiltered
- 6تركيزconcentrated in vacuo
- 7workup.DISSOLUTIONThe residue was dissolved in tetrahydrofuran (5 mL)
- 8أخرىmicrowaved in an Emry Optimizer microwave reaction vessel at 160° C., for 3 h
- 9درجة الحرارةThe mixture was then cooled
- 10تركيزconcentrated in vacuo
- 11أخرىthe residue was purified by ISCO Combiflash chromatography (40 g Silicycle, 5% to 50% ethyl acetate/hexanes)
الإجراء التجريبي
A mixture of (L)-leucine methyl ester hydrochloride (0.570 g, 3.14 mmol), (E)-4-bromo-3-(2-methyl-benzooxazol-4-yloxy)-but-2-enoic acid ethyl ester (0.970 g, 2.85 mmol) and N,N-diisopropylethylamine (0.809 g, 6.21 mmol) in acetonitrile (20 mL) in a sealed tube was heated at 100° C. for 5 h. The reaction mixture was then cooled to room temperature and ethyl acetate was added. The mixture was then filtered. The filtrate was washed successively with aqueous saturated ammonium chloride, water, and brine and then dried over sodium sulfate, filtered and concentrated in vacuo. The residue was dissolved in tetrahydrofuran (5 mL) and microwaved in an Emry Optimizer microwave reaction vessel at 160° C., for 3 h. The mixture was then cooled and concentrated in vacuo and the residue was purified by ISCO Combiflash chromatography (40 g Silicycle, 5% to 50% ethyl acetate/hexanes) to afford (S)-4-methyl-2-[4-(2-methyl-benzooxazol-4-yloxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-pentanoic acid methyl ester (0.570 g, 56%) as a brown oil.