Triethylamine → HCID 56655401, compound

Participants

Reaction Steps

A 15 mL, 1 neck flask was equipped with a magnetic stirrer, a reflux condenser and a N2 inlet. The flask was charged with benzyloxyacetic acid (166 mg, 0.001 mol) and dry dichloromethane (4 mL). To the solution was added diethyl chlorophosphate (0.36 mL, 0.0025 mol) followed by the dropwise addition of triethylamine (0.35 mL, 0.0025 mol). The reaction mixture was allowed to stir at room temperature for one hour and then 5-amino-6-bromo-1-indanone (226 mg, 0.001 mol), (weight uncorrected for a purity of about 90%) and triethylamine (0.35 mL, 0.0025 mol) was added. The reaction was refluxed for 24 hours and an aliquot was removed and analyzed by HPLC. The reaction was approximately 80% complete. The solvent was removed on the rotary evaporator affording a brown viscous residue. To the residue was added 4 mL of a 20% methanol/water mixture. A free flowing solid formed which was filtered off, washed with 4 mL of cold (0° C.) methanol and dried without heating in the vacuum oven. 220 mg (59%) of the desired benzyloxyacetamide 9 was obtained as a tan powder after drying. TLC Analysis: Rf 0.68 (50% EtOAc/hexanes). HPLC 10:90 to 90:10 CH3CN:H2O over 15 min. Hold at 90:10 for 2 min, 0.025% TFA Buffer, 1.5 mL/min, UV at 220 nm, Phenomenex Jupiter C18 column 4.6 mm×250 mm at 29° C.: (11.17 min, 94.3 A %)1H NMR (CDCl3, 400 MHz): 2.65-2.75 (m, 2H), 3.05-3.15 (m, 2H), 4.17 (s, 2H), 4.72 (s, 2H), 7.30-7.50 (m, 5H), 7.95 (s, 1H), 8.65 (s, 1H), 9.39 (br, 1H).

Provenance & Evidence