反应详情

3,4-Dichloroisatoic anhydride (147 mg, 0.634 mmol) was dissolved in DMF (2 mL). (L)-Phenylalanine methyl ester hydrochloride (150 mg, 0.697 mmol) and DMAP (85 mg, 0.697 mmol) were added and the mixture was stirred overnight at rt. The mixture was quenched with water and extracted with EtOAc (3×). The combined organic layers were washed with water, dried (MgSO4), filtered and concentrated to provide the crude product. The crude solid was purified by flash chromatography (hexanes/EtOAc) to provide the desired product as a white solid (150 mg, 68%). 1H NMR (400 MHz, CDCl3): 7.27-7.21 (m, 5H), 7.07-7.05 (m, 2H), 6.30 (d, J=7.2, 1H), 5.44 (br s, 2H), 4.95-4.90 (m, 1H), 3.71 (s, 3H), 3.22-3.09 (m, 2H).

1. customThe mixture was quenched with water
2. extractionextracted with EtOAc (3×)
3. washThe combined organic layers were washed with water
4. dry with materialdried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated
7. customto provide the crude product
8. customThe crude solid was purified by flash chromatography (hexanes/EtOAc)