反应详情

To a stirred solution of ethyl 3,4-bis(benzyloxy)-5-(dimethylcarbamoyl)-1-(4-hydroxyphenyl)-1H-pyrrole-2-carboxylate (36) (350 mg, 0.68 mmol) in THF (2 mL) at 0° C. was added 3-(methylthio)propan-1-ol (84 μL, 0.82 mmol), triphenylphosphine (214 mg, 0.82 mmol), and DIAD (159 μL, 0.82 mmol). After 2 h further portions of 3-(methylthio)propan-1-ol (84 μL, 0.82 mmol), triphenylphosphine (214 mg, 0.82 mmol) and DIAD (159 μL, 0.82 mmol) were added, and the reaction mixture was allowed to stir at RT for 4 days. The reaction mixture was quenched with water (10 mL) and extracted with EtOAc (2×20 mL), the combined organics were washed with brine (30 mL), dried (MgSO4) filtered and concentrated in vacuo. The crude product was purified by silica gel chromatography (12 g, 0-100% EtOAc in isohexane) to afford ethyl 3,4-bis(benzyloxy)-5-(dimethylcarbamoyl)-1-(4-(3-(methylthio)propoxy)phenyl)-1H-pyrrole-2-carboxylate (43) (389 mg, 85%) as a clear yellow oil: m/z 603 (M+H)+ (ES+).

1. customThe reaction mixture was quenched with water (10 mL)
2. extractionextracted with EtOAc (2×20 mL)
3. washthe combined organics were washed with brine (30 mL)
4. dry with materialdried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe crude product was purified by silica gel chromatography (12 g, 0-100% EtOAc in isohexane)