반응 #1596958

반응 방정식

4-(2-aminoethyl)benzenesulfonamide

tert-butyl 2-(2-formyl-1H-imidazol-1-yl)acetate

NaBH(OAc)3

tert-butyl glyoxalate

→

tert-butyl 2-(((1-methyl-1H-imidazol-2-yl)methyl)(4-sulfamoylphenethyl)amino)acetate

수율 44.1%

용매

DCE

AcOH

반응 조건

후처리

1. 1
   기타quenched with water
2. 2
   추출The reaction mixture was extracted with DCM
3. 3
   기타the organic layer was dried
4. 4
   농축concentrated under reduced pressure
5. 5
   기타The residue was purified by flash chromatography over silica gel

실험 절차

A solution of 4-(2-aminoethyl)benzenesulfonamide (0.70 g, 3.5 mmol), AcOH (0.20 mL) and tert-butyl 2-(2-formyl-1H-imidazol-1-yl)acetate (0.735 g, 3.5 mmol) in DCE (20 mL) was heated at 80° C. for 30 min under nitrogen. The reaction mixture was cooled to 0° C., and treated sequentially with NaBH(OAc)3 (2.25 g, 10.5 mmol) and tert-butyl glyoxalate (1.80 g). The reaction mixture was stirred at room temperature overnight and quenched with water. The reaction mixture was extracted with DCM and the organic layer was dried and concentrated under reduced pressure. The residue was purified by flash chromatography over silica gel to afford tert-butyl 2-(((1-methyl-1H-imidazol-2-yl)methyl)(4-sulfamoylphenethyl)amino)acetate (0.63 g, 35%). 1H NMR (400 MHz, DMSO-d6) δ 7.67 (d, J=8.4 Hz, 2H), 7.25 (s, 2H), 7.23 (d, J=8.4 Hz, 2H), 7.04 (d, J=1.2 Hz, 1H), 6.76 (d, J=1.2 Hz, 1H), 4.82 (s, 2H), 3.74 (s, 2H), 3.24 (s, 2H), 2.69-2.66 (m, 4H), 1.41 (s, 9H), 1.40 (s, 9H); ESMS m/z: 509 (M+H)+.

출처