Reaction #1596959

Reaction equation

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

→

2-(2-(((carboxymethyl)(4-sulfamoylphenethyl)amino)methyl)-1H-imidazol-1-yl)acetic acid

Solvents

DCM

TFA

Conditions

Workup

1. 1
   OtherThe solvent was removed under reduced pressure

Procedure

[Re(CO)3][2-(2-(((carboxymethyl)(4-sulfamoylphenethyl)amino) methyl)-1H-imidazol-1-yl)acetic acid]. To a solution tert-butyl 2-(((1-methyl-1H-imidazol-2-yl)methyl)(4-sulfamoylphenethyl)amino)acetate (40 mg, 0.079 mmol) in DCM (2.0 mL) and TFA (2.0 mL) was stirred at room temperature for 3 hrs. The solvent was removed under reduced pressure to give 2-(2-(((carboxymethyl)(4-sulfamoylphenethyl)amino)methyl)-1H-imidazol-1-yl)acetic acid. A solution of 2-(2-(((carboxymethyl)(4-sulfamoylphenethyl)amino)methyl)-1H-imidazol-1-yl)acetic acid and [NEt4]2[ReBr3(CO)3] (70 mg, 0.09 mmol) in MeOH (2.0 mL) and H2O (2.0 mL) was adjusted to pH=9 using 2 N NaOH. The mixture was stirred at 95° C. overnight in a pressure tube. The reaction mixture was purified by HPLC to give the product (20 mg, 38%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 7.76 (d, J=8.0 Hz, 2H), 7.57 (d, J=8.0 Hz, 2H), 7.36 (d, J=1.6 Hz, 1H), 7.26 (s, 2H), 7.16 (d, J=1.6 Hz, 1H), 5.05 (d, J=16.4 Hz, 1H), 4.98 (d, J=16.4 Hz, 1H), 4.73 (d, J=16.0 Hz, 1H), 4.43 (d, J=16.0 Hz, 1H), 4.00 (d, J=16.8 Hz, 1H), 3.60-3.51 (m, 3H), 3.10-3.05 (m, 2H); ESMS m/z: 667.2 (M+H)+.

Source