反应 #1881006

反应方程式

Allyliodide

2-(4-Methoxy-benzenesulfonylamino)-succinic acid 4-benzyl ester 1-tert-butyl ester

Lithium bis(trimethylsilyl)amide

→

2-Allyl-3-(4-methoxy-benzenesulfonylamino)-succinic acid 1-benzyl ester 4-tert-butyl ester

溶剂

THF

Tetrahydrofuran

THF

THF

反应条件

后处理

1. 1
   温度is maintained
2. 2
   workup.ADDITIONadded dropwise to the reaction solution
3. 3
   温度After re-cooling to −78° C
4. 4
   workup.ADDITIONare added drop-wise
5. 5
   温度to warm to −40° C.
6. 6
   其他is quenched with a NH4Cl-solution
7. 7
   其他The organic phase is separated
8. 8
   干燥dried over MgSO4
9. 9
   过滤filtered
10. 10
    其他The solvent is evaporated
11. 11
    其他the product is purified with a short flash-chromatography column

实验过程

100 ml dry Tetrahydrofuran (THF) are cooled to −78° C. 1M THF-solution of Lithium bis(trimethylsilyl)amide (47.35 ml, 47.35 mmol) are added while the temperature is maintained. 2-(4-Methoxy-benzenesulfonylamino)-succinic acid 4-benzyl ester 1-tert-butyl ester (10.1 g, 22.5 mmol) are dissolved in 45 ml THF and added dropwise to the reaction solution. The reaction mixture is allowed to stir for 1 h and then warmed briefly to −40° C. After re-cooling to −78° C. Allyliodide (3.1 ml, 33.8 mmol) dissolved in 30 ml THF are added drop-wise. The reaction mixture is allowed to warm to −40° C. and is quenched with a NH4Cl-solution. The organic phase is separated dried over MgSO4 and filtered. The solvent is evaporated and the product is purified with a short flash-chromatography column. Hexane/Ethylacetate (9:1): Cal. 489.6 Found. (M)+ 490.

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