Hydrochloric Acid → HCID 58340637, compound

Participants

Reaction Conditions

Reaction Steps

{Carboxymethyl-[4-(4-bromo-phenoxy)-benzenesulphonyl]-amino}-acetic acid (4d) (1.90 g, 4.30 mmol) was dissolved in dry THF (50 mL). ECF (0.35 mL, 3.70 mmol), and NMM (0.40 mL, 3.70 mmol) were added and stirred for 40 min at 0° C. NH2OH×HCl (0.30 g, 4.30 mmol) and KOH (0.24 g, 4.30 mmol) were dissolved in dry MeOH (20 mL) and stirred at 0° C. for 30 min. The solids were filtered off, and the THF solution was added dropwise to the methanol filtrate and stirred for 2 h at 0° C. The reaction mixture was filtered, the solvent evaporated, and the residue dissolved in H2O (20 mL). After adjusting the pH to 1-2, the aqueous layer was extracted with EtOAc (3×30 mL). The combined organic layers were dried over MgSO4 and evaporated in vacuo to yield the pure product as white crystals. Yield: 1.80 g, 3.90 mmol, 91%. 1H NMR (D2O): δ 7.7 (d, J=8.2 Hz, 2H, ArH), 7.5 (d, J=8.8 Hz, 2H, ArH), 7.0 (d, J=8.8 Hz, 2H, ArH), 4.0 (s, 4H, CH2COOH). ESI-MS calcd for C16H15BrN2O7S 457.98 [M-H]−, obsd 459.27.

Provenance & Evidence