反応 #65536

反応方程式

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

収率 81.3%

溶媒

water

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

dimethylformamide

反応条件

後処理

1. 1
   その他at -5°
2. 2
   その他∫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
   その他Tetrahydrofuran was evaporated under reduced pressure
7. 7
   その他to give
8. 8
   その他precipitates
9. 9
   ろ過The precipitates were collected by filtration
10. 10
    洗浄washed with water and diisopropyl ether successively
11. 11
    乾燥dried over phosphorus pentoxide

実験手順

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).

出典