Reacción #476403

Ecuación de reacción

HCl

compound

1-[({[(1R,2R)-2-Pent-4-en-1-ylcyclopentyl]oxy}carbonyl)oxy]pyrrolidine-2,5-dione

compound

Ethyl (2S,6S,12Z,13aS,14aR,16aS)-6-amino-2-{[(4-bromophenyl)sulfonyl]oxy}-5,16-dioxo-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylate hydrochloride

Et3N

→

Ethyl (2S,6S,12Z,13aS,14aR,16aS)-2-{[(4-bromophenyl)sulfonyl]oxy}-5,16-dioxo-6-[({[(1R,2R)-2-pent-4-en-1-ylcyclopentyl]oxy}carbonyl)amino]-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylate

Disolventes

EtOAc

MeCN

MeCN

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadothe organics were washed with brine
2. 2
   Secadodried over Na2SO4
3. 3
   Filtraciónfiltered
4. 4
   Concentraciónconcentrated
5. 5
   OtroThe crude material was purified by silica gel chromatography (gradient elution 0 to 100% EtOAc in hexane)

Procedimiento

To a solution of the compound from Step 1 (300 mg, 0.46 mmol) in MeCN (0.5 mL) was added Et3N (0.19 mL, 1.36 mmol). A solution of the compound from Step 2 (150 mg, 0.51 mmol) in MeCN (1.5 mL) was added, and the reaction mixture was stirred at RT for 1 hour. The reaction mixture was worked up with EtOAc and 1M HCl, and the organics were washed with brine, dried over Na2SO4, filtered and concentrated. The crude material was purified by silica gel chromatography (gradient elution 0 to 100% EtOAc in hexane). LCMS (M+H)+=792.0.

Fuente