1,4-Dioxane → (2-(2-Benzyloxycarbonylamino-ethoxy)-ethyl)-carbamic acid benzyl ester

Participants

Reaction Steps

To a solution of 300 mg (80% purity, 0.271 mmol) of the 6-octyloxy-2-naphthoyl starting material above prepared, 1.4 grams (7.18 mmol) of 2-(N-benzyloxycarbonylamino)ethanol and 62.9 mg (0.271 mmol) of (1S)-(+)-10-camphorsulfonic acid in 10 ml anhydrous dioxane and 1 mL anhydrous DMF was stirred at 25° C. HPLC analysis using 65% CH3CN/H2O at 1.5 mL/min with detection at 210 and 277 nm indicated. after 18 hours a greater than 95 percent conversion to a less polar product (tR =3.36 min). The reaction was quenched with 1M NaHC03, the reaction mixture diluted with water and subjected to reverse-phase flash chromatography eluting with 40-60 percent CH3CN/H2O in 10% step gradients to obtain after lyophilization of the 60 percent fractions, ether ##STR10##

Provenance & Evidence