反应详情

温度

0 °C

To a mixture of 3-chloro-N1-phenylbenzene-1,2-diamine (1.72 g, 7.87 mmol), (S)-2-tertbutoxycarbonylaminopropionic acid (1.64 g, 8.65 mmol), HOAt (1.18 g, 8.65 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (1.66 g, 8.65 mmol) in DCM (40 mL) cooled to 0° C. under a nitrogen atmosphere was added Et3N (3.3 mL, 0.0236 mol). The reaction mixture was stirred at 0° C. for 5 min, then slowly warmed to RT and stirring was continued for 16 h. The resulting mixture was partitioned between DCM and a saturated solution of NaHCO3. The organic layer was washed with brine, then dried (Na2SO4) and concentrated in vacuo. The residue thus obtained was purified column chromatography (Si—PCC, gradient 0-2% 2M NH3/MeOH in DCM) affording [(S)-1-(2-Chloro-6-phenylaminophenylcarbamoyl)ethyl]carbamic acid tertbutyl ester as an off-white solid (1.60 g, 52% over three steps). LCMS: RT 3.75 min [M+H]+ 390.2.

1. temperatureslowly warmed to RT
2. stirringstirring
3. waitwas continued for 16 h
4. customThe resulting mixture was partitioned between DCM
5. washThe organic layer was washed with brine
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated in vacuo
8. customThe residue thus obtained
9. customwas purified column chromatography (Si—PCC, gradient 0-2% 2M NH3/MeOH in DCM)