반응 #2352354

반응 방정식

3,4-Dichloroisatoic anhydride

(L)-Phenylalanine methyl ester hydrochloride

→

desired product

수율 68.0%

2-(2-Amino-4,5-dichloro-benzoylamino)-3-phenyl-propionic acid methyl ester

수율 68.0%

용매

DMF

반응 조건

후처리

1. 1
   기타The mixture was quenched with water
2. 2
   추출extracted with EtOAc (3×)
3. 3
   세척The combined organic layers were washed with water
4. 4
   건조dried (MgSO4)
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   기타to provide the crude product
8. 8
   기타The crude solid was purified by flash chromatography (hexanes/EtOAc)

실험 절차

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).

출처