反应详情

The N-benzoyl-cis-4-phenylthio-L-proline is heated on a steam bath and 0.5 liters of glacial acetic acid are added. The mixture is swirled and 0.5 liters of water followed by 100 ml. of concentrated sulfuric acid are added. The turbid mixture is heated at reflux at an oil bath temperature of about 125° and maintained at reflux until the reaction is completed. The reaction liquid is cooled to room temperature and 0.75 liters of isobutyl acetate and 3 kg. of cracked ice are added with brisk agitation. 50 g. of concentrated aqueous sodium hydroxide solution are added and the product is collected and washed with methanol. The product is further purified by dissolution in aqueous sodium hydroxide, treatment with activated carbon, filtration, and careful crystallization with HCl. The crystals are collected, washed with water, and dried to yield cis-4-phenyl-thio-L-proline as a white crystalline powder; m.p. 240° (d); [α]D23 -118° (C=1, N sodium hydroxide).

1. temperatureThe turbid mixture is heated
2. temperatureat reflux at an oil bath temperature of about 125°
3. temperaturemaintained
4. temperatureat reflux until the reaction
5. customThe reaction liquid
6. additionof cracked ice are added with brisk agitation
7. customthe product is collected
8. washwashed with methanol
9. customThe product is further purified by dissolution in aqueous sodium hydroxide
10. filtrationtreatment with activated carbon, filtration, and careful crystallization with HCl
11. customThe crystals are collected
12. washwashed with water
13. customdried