Tris(hydroxymethyl)aminomethane → HCID 131716350, compound

Participants

Reaction Conditions

Reaction Steps

A 1000 ml round bottom flask was charged with 63.4 g (0.134 mole) of 5(6)-carboxyfluorescein N-hydroxysuccinimide ester, and 16.2 g (0.134 mole), of tris(hydroxymethyl)aminomethane, and 33.8 g (0.335 mole) of triethylamine. The contents of the flask were dissolved in 200 ml of dry dimethylformamide and stirred under nitrogen for 24 hours. A trace of 4-dimethylaminopyridine was added and the reaction was heated under nitrogen for another hour at 70° C. At the end of this period the reaction appeared complete by thin layer chromatography. The solvent was reduced down to a total volume of 200 ml of a dark red oily solution. This material was purified on preparatory HPLC apparatus using silica gel column and an elution solvent of acetic acid:2-propanol:ethyl acetate (2 8:70). The yield obtained was 20.5 g (32%). The desired structure was confirmed by 1H-NMR (CD3OD) which gave the following chemical shifts:

Provenance & Evidence