Реакция #5492

Уравнение реакции

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

4-Methylmorpholine

Ethyl chloroformate

→

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

Растворители

tetrahydrofuran

methylene chloride

Условия реакции

Обработка

1. 1
   ФильтрацияThe reaction is then filtered
2. 2
   Концентрированиеthe filtrate is concentrated
3. 3
   Другоеto give a yellow oil
4. 4
   Другоеanhydrous ammonia gas is bubbled through the solution for 1 hour
5. 5
   workup.STIRRINGthe reaction is stirred an additional 1 hour
6. 6
   ДругоеThe solvent is evaporated
7. 7
   Другоеthe residue is partitioned between ethyl acetate and water
8. 8
   ЭкстракцияThe aqueous layer is extracted several times with ethyl acetate
9. 9
   Сушкаthe combined organic layers are dried (Na2SO4)
10. 10
    Другоеthe solvent is evaporated

Методика

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.

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