Реакция #1596956

Уравнение реакции

4-(2-aminoethyl)benzenesulfonamide

1-methyl-1H-imidazole-2-carboxaldehyde

NaBH(OAc)3

tert-butyl glyoxalate

→

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

Растворители

DCE

AcOH

Условия реакции

Обработка

1. 1
   Другоеquenched with water
2. 2
   ЭкстракцияThe reaction mixture was then extracted with DCM
3. 3
   Другоеthe organic layer was dried
4. 4
   Концентрированиеconcentrated under reduced pressure
5. 5
   ДругоеThe residue obtained
6. 6
   Другоеwas purified by flash chromatography over silica gel to tert-butyl 2-(((1-methyl-1H-imidazol-2-yl)methyl)(4-sulfamoylphenethyl)amino)acetate (0.63 g, 22%)

Методика

A solution of 4-(2-aminoethyl)benzenesulfonamide (1.40 g, 7.0 mmol), AcOH (0.30 mL) and 1-methyl-1H-imidazole-2-carboxaldehyde (0.77 g, 7.0 mmol) in DCE (40 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 (4.45 g, 21 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 then extracted with DCM and the organic layer was dried and concentrated under reduced pressure. The residue obtained was purified by flash chromatography over silica gel to tert-butyl 2-(((1-methyl-1H-imidazol-2-yl)methyl)(4-sulfamoylphenethyl)amino)acetate (0.63 g, 22%). 1H NMR (400 MHz, DMSO-d6) δ 7.65 (d, J=8.4 Hz, 2 H), 7.26 (s, 2 H), 7.21 (d, J=8.0 Hz, 2 H), 6.99 (d, J=0.8 Hz, 1 H), 6.73 (d, J=0.8 Hz, 1 H), 3.76 (s, 2 H), 3.38 (s, 3 H), 3.28 (s, 2 H), 2.79 (t, J=7.2 Hz, 2 H), 2.69 (t, J=6.8 Hz, 2 H), 1.40 (s, 9 H); ESMS m/z: 409 (M+H)+.

Источник