Reacción #325247

Ecuación de reacción

4-bromobenzene-1-sulfonyl chloride

(2S,6S,13aS,14aR,16aS,Z)-ethyl 6-(tert-butoxycarbonylamino)-2-hydroxy-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxylate

DABCO

→

title compound

(2S,6S,13aS,14aR,16aS,Z)-ethyl 2-(4-bromophenylsulfonyloxy)-6-(tert-butoxycarbonylamino)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxylate

Disolventes

toluene

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONAfter the addition
2. 2
   Otrowas quenched with 10% aqueous sodium carbonate
3. 3
   workup.ADDITIONTetrahydrofuran was added
4. 4
   Lavadothe mixture was washed with 0.5 M HCl, water
5. 5
   SecadoThe organic layer was dried over anhydrous magnesium sulfate
6. 6
   Filtraciónfiltered
7. 7
   Otroevaporated under reduced pressure
8. 8
   Otrodried

Procedimiento

A solution of (2S,6S,13aS,14aR,16aS,Z)-ethyl 6-(tert-butoxycarbonylamino)-2-hydroxy-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxylate and DABCO in toluene was stirred at room temperature (rt). To this solution was added a solution of 4-bromobenzene-1-sulfonyl chloride in toluene. After the addition was complete the reaction mixture was quenched with 10% aqueous sodium carbonate and the mixture stirred for 15 min. Tetrahydrofuran was added and the mixture was washed with 0.5 M HCl, water, and then saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure and dried to provide the title compound.

Fuente