反应 #1881012

反应方程式

Benzyl alcohol

Tripropylamine

1-(4-Methoxy-benzenesulfonyl)-2,3,4,7-tetrahydro-1H-azepine-2,3-dicarboxylic acid 2-tert-butyl ester

Diphenyl phosphoryl azide

→

3-Benzyloxycarbonylamino-1-(4-methoxy-benzenesulfonyl)-2,3,4,7-tetrahydro-1H-azepine-2-carboxylic acid tert-butyl ester

溶剂

Ethylacetate

Dioxane

反应条件

后处理

1. 1
   温度the reaction is gradually heated to 60° C. for 3 h
2. 2
   温度to cool to room temperature
3. 3
   温度the reaction solution is heated to 60° C. over night
4. 4
   洗涤washed with 2 M Citric Acid and Water
5. 5
   其他The organic phase is separated
6. 6
   干燥dried with MgSO4
7. 7
   过滤filtrated
8. 8
   其他The solvent is evaporated
9. 9
   其他the remaining oil is purified by flash-chromatography, Hexane/Ethylacetate (2:1)

实验过程

The reaction is performed under an Argon athmosphere. 1-(4-Methoxy-benzenesulfonyl)-2,3,4,7-tetrahydro-1H-azepine-2,3-dicarboxylic acid 2-tert-butyl ester (300 mg, 0.73 mmol) is dissolved in 4 ml Dioxane (dry). Tripropylamine (TPA) (98 μl, 0.73 mmol) is added and the reaction is stirred for 15 minutes at RT. Diphenyl phosphoryl azide (157 μl, 0.73 mmol) is added and the reaction is gradually heated to 60° C. for 3 h. The reaction is then allowed to cool to room temperature. Benzyl alcohol (235 μl, 2.2 mmol) is added and the reaction solution is heated to 60° C. over night. The reaction solution is diluted with Ethylacetate and washed with 2 M Citric Acid and Water. The organic phase is separated, dried with MgSO4 and filtrated. The solvent is evaporated and the remaining oil is purified by flash-chromatography, Hexane/Ethylacetate (2:1): Cal. 516.6, found (M)+ 517.

来源