Реакция #65535

Уравнение реакции

(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

Выход 41.3%

Растворители

tetrahydrofuran

Условия реакции

Обработка

1. 1
   Другоеthe mixture was evaporated
2. 2
   ЭкстракцияThe residue was extracted with dichloromethane
3. 3
   Промывкаwashed with water and brine successively
4. 4
   Сушкаdried over magnesium sulfate
5. 5
   ДругоеThe organic layer was evaporated
6. 6
   Промывкаeluted with a mixture of dichloromethane and acetone (4:1V/V)

Методика

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).

Источник