反応 #65535

反応方程式

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

2-aminoethanethiol

→

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

収率 41.3%

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   その他the mixture was evaporated
2. 2
   抽出The residue was extracted with dichloromethane
3. 3
   洗浄washed with water and brine successively
4. 4
   乾燥dried over magnesium sulfate
5. 5
   その他The organic layer was evaporated
6. 6
   洗浄eluted with a mixture of dichloromethane and acetone (4:1V/V)

実験手順

To a solution of (2S, 4R)-2-cyano-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl) pyrrolidine (2 g) in tetrahydrofuran (40 ml) was added 2-aminoethanethiol (630 mg) at ambient temperature. After stirring for 24 hours at the same temperature, the mixture was evaporated. The residue was extracted with dichloromethane, washed with water and brine successively, and dried over magnesium sulfate. The organic layer was evaporated, and then the obtained oil was subjected to a column chromatography on silica gel and eluted with a mixture of dichloromethane and acetone (4:1V/V) to give (2S,4R)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)-2-(2-thiazolin-2-yl) pyrrolidine (0.96 g).

出典