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

Participants

Reaction Steps

Title compound 11a 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 410 mg (3.20 mmol) of sodium 2-aminoethanesulfinate (5) in approximately one (1) mL of degassed water was reacted with a solution of 4-acetamidophenyl 4-nitrophenyl carbonate (3) (1.01 g, 3.19 mmol) in 10 mL of acetonitrile (MeCN). After work-up procedures, the aqueous layer was lyophilized off to afford 910 mg (˜quantitative yield) of the crude 2-((4-acetamidophenoxy)carbonylamino)ethanesulfinic acid (11a) which was used directly and without further isolation or purification procedures in the next step. The material thus obtained was contaminated with some sodium chloride (NaCl) and/or other sodium salts. 1H NMR (300 MHz, D2O): δ 7.22 (d, J=9.0 Hz, 2H), 6.93 (d, J=9.0 Hz, 2H), 3.31 (t, J=6.6 Hz, 2H), 2.42 (t, J=6.6 Hz, 2H), 1.96 (s, 3H). LC/MS (ESI): m/z=287.1 [M+H]+.

Provenance & Evidence