反应 #5492

反应方程式

Trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxylic acid

4-Methylmorpholine

Ethyl chloroformate

→

trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxamide

溶剂

tetrahydrofuran

methylene chloride

反应条件

后处理

1. 1
   过滤The reaction is then filtered
2. 2
   浓缩the filtrate is concentrated
3. 3
   其他to give a yellow oil
4. 4
   其他anhydrous ammonia gas is bubbled through the solution for 1 hour
5. 5
   workup.STIRRINGthe reaction is stirred an additional 1 hour
6. 6
   其他The solvent is evaporated
7. 7
   其他the residue is partitioned between ethyl acetate and water
8. 8
   萃取The aqueous layer is extracted several times with ethyl acetate
9. 9
   干燥the combined organic layers are dried (Na2SO4)
10. 10
    其他the solvent is evaporated

实验过程

Trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxylic acid (0.30 g, 1.05 mmol) is dissolved in tetrahydrofuran (5.0 mL). 4-Methylmorpholine (0.14 mL, 1.05 mmol) is then added, and the reaction is cooled to -20° C. Ethyl chloroformate (0.1 mL, 1.05 mmol) is then added, and the reaction is stirred at -20° C. for 30 minutes. The reaction is then filtered, and the filtrate is concentrated to give a yellow oil. This oil is dissolved in methylene chloride (20.0 mL), and anhydrous ammonia gas is bubbled through the solution for 1 hour. The bubbling is stopped, and the reaction is stirred an additional 1 hour. The solvent is evaporated, and the residue is partitioned between ethyl acetate and water. The aqueous layer is extracted several times with ethyl acetate, the combined organic layers are dried (Na2SO4), and the solvent is evaporated to give trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxamide, MS:M+1=287.

来源