Sodium Bicarbonate → Disodium (2R)-2-((4-acetamidophenoxy)carbonylamino)-3-sulfonatopropanoate

Participants

Reaction Steps

Disodium (2R)-2-((4-acetamidophenoxy)carbonylamino)-3-sulfonatopropanoate (13) was prepared following the General Procedure for the Preparation of Alkali Metal Salts (Procedure B). (2R)-2-[(4-Acetamidophenoxy)carbonylamino]-3-sulfo-propanoic acid (13a) (83 mg, 0.24 mmol), dissolved in 2.0 mL of water, was reacted with 40.3 mg (0.48 mmol; 2.0 eq.) of sodium hydrogencarbonate (NaHCO3) dissolved in 0.5 mL of water. The mixture was sonicated with agitation for three (3) minutes, frozen, and the solvents lyophilized off to afford 88 mg (95% yield) of the title compound (13) as a colorless solid. 1H NMR (300 MHz, D2O): δ=7.21 (d, J=8.7, 2H), 6.97 (d, J=9.0, 2H), 4.36-4.32 (m, 1H), 3.28-3.22 (m, 1H), 3.12-3.04 (m, 1H), 1.96 (s, 3H) ppm. LC/MS: LC/MS (ESI): m/z=347.0 [M+H]+, 714.7 [2M+Na]+.

Provenance & Evidence