반응 #65536

반응 방정식

sodium hydroxide

4-methylthiosemicarbazide

phosphorus oxychloride

(2S,4R)-2- carboxy-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

→

(2S, 4R)-4-methanesulfonyloxy -2-(4-methylthiosemicarbazidocarbonyl)-1-(4-nitrobenzyloxycarbonyl) pyrrolidine

수율 81.3%

용매

water

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

dimethylformamide

반응 조건

후처리

1. 1
   기타at -5°
2. 2
   기타∫5° C.
3. 3
   workup.STIRRINGby stirring at the same temperature for 30 minutes
4. 4
   workup.STIRRINGwith stirring
5. 5
   workup.STIRRINGThe mixture was stirred at the same condition for 2 hours
6. 6
   기타Tetrahydrofuran was evaporated under reduced pressure
7. 7
   기타to give
8. 8
   기타precipitates
9. 9
   여과The precipitates were collected by filtration
10. 10
    세척washed with water and diisopropyl ether successively
11. 11
    건조dried over phosphorus pentoxide

실험 절차

To a mixture of dimethylformamide (2.9 ml) and tetrahydrofuran (6 ml) was dropwise added phosphorus oxychloride (2.8 ml) at -5°∫5° C. and the mixture was stirred at the same temperature for 30 minutes. To the mixture was added a solution of (2S,4R)-2- carboxy-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (9.65 g) in tetrahydrofuran (20 ml) at -5°∫5° C., followed by stirring at the same temperature for 30 minutes. The mixture was dropwise added to a solution of 4-methylthiosemicarbazide (25 g) in a mixture of water (200 ml) and tetrahydrofuran (200 ml) at 0°-10° C. with stirring, keeping the pH between 8-9 with 1N aqueous sodium hydroxide. The mixture was stirred at the same condition for 2 hours. Tetrahydrofuran was evaporated under reduced pressure to give precipitates. The precipitates were collected by filtration, washed with water and diisopropyl ether successively, and dried over phosphorus pentoxide to give (2S, 4R)-4-methanesulfonyloxy -2-(4-methylthiosemicarbazidocarbonyl)-1-(4-nitrobenzyloxycarbonyl) pyrrolidine (9.61 g).

출처