Reacción #1596956

Ecuación de reacción

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

Disolventes

DCE

AcOH

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroquenched with water
2. 2
   ExtracciónThe reaction mixture was then extracted with DCM
3. 3
   Otrothe organic layer was dried
4. 4
   Concentraciónconcentrated under reduced pressure
5. 5
   OtroThe residue obtained
6. 6
   Otrowas 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%)

Procedimiento

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)+.

Fuente