Water → 2-((4-Acetamidophenoxy)carbonylamino)ethanesulfonic acid

Participants

Reaction Steps

((4-Acetamidophenoxy)carbonylamino)ethanesulfonic acid (12a) was prepared according to the General Method for the Reaction of Alkali Metal Salts of Amino Acid Derivatives with 4-Acetamidophenyl 4-Nitrophenyl carbonate (3). A solution of 511 mg (3.48 mmol) of sodium 2-aminoethanesulfonate (7) in approximately one (1) mL of degassed water was reacted with a solution of 4-acetamidophenyl 4-nitrophenyl carbonate (3) (1.10 g, 3.48 mmol) dissolved in 5 mL of acetonitrile (MeCN). After work-up procedures, the aqueous layer was lyophilized off to afford 1.0 g (˜quantitative yield) of the crude 2-((4-acetamidophenoxy)carbonylamino)ethanesulfonic acid (12a) which was used directly and without further isolation or purification procedures. The material thus obtained was contaminated with some sodium chloride (NaCl) and other sodium salts. 1H NMR (300 MHz, D2O): δ 7.22 (d, J=9.0 Hz, 2H), 6.94 (d, J=8.7 Hz, 2H), 3.40 (t, J=6.6 Hz, 2H), 2.95 (t, J=6.6 Hz, 2H), 1.96 (s, 3H). LC/MS (ESI): m/z=303.0 [M+H]+, 602.8 [2M−H]−.

Provenance & Evidence