反応 #65553

反応方程式

(2S, 4R)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl) -2-thiocarbamoylpyrrolidine

ethyl bromopyruvate

→

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

溶媒

dichloromethane

ethanol

反応条件

後処理

1. 1
   その他the mixture was evaporated
2. 2
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
3. 3
   洗浄washed with saturated sodium bicarbonate and brine successively
4. 4
   その他The dried organic layer was evaporated
5. 5
   workup.DISSOLUTIONthe residue was dissolved in tetrahydrofuran (15 ml) and in sodium hydroxide (15 ml)
6. 6
   workup.STIRRINGAfter stirring at 35°-45° C. for 1 hour
7. 7
   その他the mixture was evaporated
8. 8
   workup.ADDITIONpoured into ethyl acetate
9. 9
   workup.ADDITIONTo this mixture was added 1N hydrochloric acid (20 ml)
10. 10
    その他organic layer was separated
11. 11
    洗浄washed with brine
12. 12
    その他The dried organic layer was evaporated

実験手順

To a solution of (2S, 4R)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl) -2-thiocarbamoylpyrrolidine (2.0 g) in dichloromethane (40 ml) was added a solution of ethyl bromopyruvate (1.04 ml) in absolute ethanol (10 ml) at 0° C. After stirring at room temperature for 2 hours, the mixture was evaporated. The residue was dissolved in ethyl acetate, and washed with saturated sodium bicarbonate and brine successively. The dried organic layer was evaporated and the residue was dissolved in tetrahydrofuran (15 ml) and in sodium hydroxide (15 ml). After stirring at 35°-45° C. for 1 hour, the mixture was evaporated and poured into ethyl acetate. To this mixture was added 1N hydrochloric acid (20 ml), and then organic layer was separated, and washed with brine. The dried organic layer was evaporated to give (2S,4R)-2- (4-carboxythiazol-2-yl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl) pyrrolidine (1.54 g).

出典