تفاعل #1596958

معادلة التفاعل

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

المردود 44.1%

المذيبات

DCE

AcOH

ظروف التفاعل

المعالجة

1. 1
   أخرىquenched with water
2. 2
   استخلاصThe reaction mixture was extracted with DCM
3. 3
   أخرىthe organic layer was dried
4. 4
   تركيزconcentrated under reduced pressure
5. 5
   أخرىThe residue was purified by flash chromatography over silica gel

الإجراء التجريبي

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)+.

المصدر