Reacción #84055

Ecuación de reacción

Serotonin hydrochloride

Ethylchloroformate

prostaglandin F2α

triethylamine

→

(Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-((E)-(S)-3-hydroxy-oct-1-enyl)-cyclopentyl]-hept-5-enoic acid [2-(5-hydroxy-1H-indol-3-yl)-ethyl]-amide

Rendimiento 68.0%

Disolventes

ethyl acetate

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas warmed to room temperature
2. 2
   workup.STIRRINGstirred for 16 hours
3. 3
   Lavadowashed with HCl (1 N), saturated sodium bicarbonate, and brine
4. 4
   SecadoThe organic portion was dried (MgSO4)
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated in vacuo
7. 7
   workup.ADDITIONThe residue was diluted with methanol and pyridinium p-toluenesulfonate (PPTs) (100 mg)
8. 8
   workup.ADDITIONwas added
9. 9
   workup.STIRRINGthe solution was stirred for 24 hours
10. 10
    OtroThe solvent was then removed in vacuo
11. 11
    workup.ADDITIONthe residue was diluted with ethyl acetate
12. 12
    Lavadowashed with HCl (1 N), saturated sodium bicarbonate, and brine
13. 13
    SecadoThe organic portion was dried (MgSO4)
14. 14
    Filtraciónfiltered
15. 15
    Concentraciónconcentrated in vacuo

Procedimiento

A solution of the protected prostaglandin F2α (500 mg, 0.825 mmol) in CH2Cl2 (4.5 mL) was treated with triethylamine (290 μL, 2.06 mmol) with stirring and cooled to 0° C. Ethylchloroformate (87 μL, 0.907 mmol) was then added and after 15 minutes the reaction was warmed to room temperature. Serotonin hydrochloride (211 mg, 0.99 mmol) was added and stirred for 16 hours. The reaction was then diluted with ethyl acetate and washed with HCl (1 N), saturated sodium bicarbonate, and brine. The organic portion was dried (MgSO4), filtered and concentrated in vacuo. The residue was diluted with methanol and pyridinium p-toluenesulfonate (PPTs) (100 mg) was added and the solution was stirred for 24 hours. The solvent was then removed in vacuo, and the residue was diluted with ethyl acetate and washed with HCl (1 N), saturated sodium bicarbonate, and brine. The organic portion was dried (MgSO4), filtered and concentrated in vacuo. Flash column chromatography (silica gel, 19:1 ethyl acetate:methanol) gave (Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-((E)-(S)-3-hydroxy-oct-1-enyl)-cyclopentyl]-hept-5-enoic acid [2-(5-hydroxy-1H-indol-3-yl)-ethyl]-amide (Compound 3) (287 mg, 68%).

Fuente