反应详情

温度

0 °C

1-Acetylguanidine (7.20 g, 71.0 mmol) was dissolved in THF (100 mL). The solution was cooled to 0° C. and NaH (1.90 g, 80.0 mmol) was added to the reaction in small batches over 5 mins. Next, 2-ethoxythiocarbonyl-pyrrolidine-1-carboxylic acid benzyl ester (19.6 g, 66.9 mmol) in THF (50 mL) was added to the reaction dropwise over 30 minutes while maintaining the temperature between 0-5° C. The reaction was allowed to return to room temperature, while stirring an additional 12 hours. The product was precipitated by addition of petroleum ether. The organic layer was decanted off and the solid was retained and redissolved in water (300 mL). The pH was adjusted to pH=3 by addition of acetic acid. The resulting solution was transferred to a separatory funnel and extracted with DCM (3×250 mL). The organic layers were combined, dried over MgSO4 and concentrated under vacuo to afford 13.0 g (56%) of 2-(N′-acetyl-guanidinocarbothioyl)-pyrrolidine-1-carboxylic acid benzyl ester.

1. temperaturewhile maintaining the temperature between 0-5° C
2. customto return to room temperature
3. customThe product was precipitated by addition of petroleum ether
4. customThe organic layer was decanted off
5. dissolutionredissolved in water (300 mL)
6. additionThe pH was adjusted to pH=3 by addition of acetic acid
7. customThe resulting solution was transferred to a separatory funnel
8. extractionextracted with DCM (3×250 mL)
9. dry with materialdried over MgSO4
10. concentrationconcentrated under vacuo