反应详情

温度

0 °C

Thioacetic acid (4 mL), which had been cooled to 0° C., was added to a mixture of 2-(cis4-tert-butoxycarbonylamino-cyclopent-2-enylmethyl)-acrylic acid ethyl ester (0.56 g, 1.9 mmol) and triethyl amine (0.28 mL, 2.0 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 30 min, at room temperature for 19 h and then poured onto ice-water (400 mL). The aqueous layer was extracted with CH2Cl2. The organic phase was washed with saturated NaHCO3, dried and concentrated under reduced pressure to give 1.7 g of the crude product. Purification by flash chromatography (CH2Cl2/EtOAc: 1/0→68/32) afforded 2-acetylsulfanylmethyl-3-(cis4-tert-butoxycarbonylamino-cyclopent-2-enyl)-propionic acid ethyl ester (0.46 g, 65%).

1. additionpoured onto ice-water (400 mL)
2. extractionThe aqueous layer was extracted with CH2Cl2
3. washThe organic phase was washed with saturated NaHCO3
4. customdried
5. concentrationconcentrated under reduced pressure
6. customto give 1.7 g of the crude product
7. customPurification by flash chromatography (CH2Cl2/EtOAc: 1/0→68/32)