反应详情

温度

100 °C

A mixture of the (S)-2-{[2-(2-1H-Indazol-4-yl-acetylamino)-4-methyl-thiazole-5-carbonyl]-amino}-3-[(thiophene-2-carbonyl)-amino]-propionic acid (75.3 mg, 0.147 mmole), 3,3-dimethyl-1-butanol (1 mL, 8.054 mmol) and p-toluenesulfonic acid monohydrate (14.1 mg, 0.0741 mmol) was heated at 100° C. for 2½ hours. The reaction is cooled, neutralized and extracted with ethyl acetate (3×15 mL). The organic layers were combined, washed with brine (50 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The resulting crude compound was purified by flash chromatography (80% EtOAc in hexanes) to give (S)-2-{[2-(2-1H-Indazol-4-yl-acetylamino)-4-methyl-thiazole-5-carbonyl]-amino}-3-[(thiophene-2-carbonyl)-amino]propionic acid 3,3-dimethyl-butyl ester (31.5 mg, 35.9%) as a white solid. MS m/e 597.7 (M+H+).

1. temperatureThe reaction is cooled
2. extractionextracted with ethyl acetate (3×15 mL)
3. washwashed with brine (50 mL)
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe resulting crude compound was purified by flash chromatography (80% EtOAc in hexanes)