反应详情

温度

0 °C

To a mixture of N2-phenylpyridine-2,3-diamine (2.00 g, 0.011 mol), (S)-2-tertbutoxycarbonylaminopropionic acid (3.06 g, 0.0162 mol), HOBt (2.19 g, 0.0162 mol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (3.10 g, 0.0162 mol) in DCM (80 mL) cooled to 0° C. under a nitrogen atmosphere was added Et3N (4.5 mL, 0.0324 mol). The reaction mixture was stirred at 0° C. for 5 min, then slowly warmed to RT and stirring was continued for 20 h. The resulting mixture was partitioned between EtOAc and a saturated solution of NaHCO3. The aqueous phase was further extracted with EtOAc and the combined organic layers were washed with brine, then dried (Na2SO4) and concentrated in vacuo. The residue thus obtained was purified column chromatography (Si—PCC, gradient 0-5% 2M NH3/MeOH in DCM) affording [(S)-1-(2-phenylaminopyridin-3-ylcarbamoyl)ethyl]carbamic acid tertbutyl ester as a pale pink solid (2.05 g, 4.56 mmol). LCMS: RT 3.75 min [M+H]+ 390.2

1. temperatureslowly warmed to RT
2. stirringstirring
3. waitwas continued for 20 h
4. customThe resulting mixture was partitioned between EtOAc
5. extractionThe aqueous phase was further extracted with EtOAc
6. washthe combined organic layers were washed with brine
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated in vacuo
9. customThe residue thus obtained
10. customwas purified column chromatography (Si—PCC, gradient 0-5% 2M NH3/MeOH in DCM)