Hydrochloric Acid → N-Fmoc-iminodiacetic acid

Participants

Reaction Steps

Iminodiacetic acid (2.19 g, 16.5 mmol, Sigma Chemical Co., St. Louis, Mo.) was dissolved in a mixture of 1 M sodium bicarbonate (40 ml) and acetone (30 ml). 9-Fluorenemethyl chloroformate (2.0 g, 7.7 mmol) was dissolved in acetone (10 ml) and added to the above solution. After 6 hours reaction, the mixture was treated with brine, acidified with 1N HCl, and extracted with ethyl acetate. The yield was 2.38 g (87%), mp 213°-215.5° C. The mass spectrum (CI-NH3) showed a peak at 373 corresponding to m+1+NH3. Analysis (C19H17N06): calc. 64.22% C, 4.82% H, 3.94% N; found 64.15% C, 4.83% H, 3.909% N.

Provenance & Evidence