Reacción #5492

Ecuación de reacción

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

4-Methylmorpholine

Ethyl chloroformate

→

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

Disolventes

tetrahydrofuran

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónThe reaction is then filtered
2. 2
   Concentraciónthe filtrate is concentrated
3. 3
   Otroto give a yellow oil
4. 4
   Otroanhydrous ammonia gas is bubbled through the solution for 1 hour
5. 5
   workup.STIRRINGthe reaction is stirred an additional 1 hour
6. 6
   OtroThe solvent is evaporated
7. 7
   Otrothe residue is partitioned between ethyl acetate and water
8. 8
   ExtracciónThe aqueous layer is extracted several times with ethyl acetate
9. 9
   Secadothe combined organic layers are dried (Na2SO4)
10. 10
    Otrothe solvent is evaporated

Procedimiento

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.

Fuente