Acetic Acid → HCID 66756970, compound

Participants

Reaction Steps

Ethyl glyoxlate is added to a solution of 2-(4-amino-3-benzyloxybenzyl)-6-benzyloxybenzonitrile (0.281 g, 0.668 mmol), ACN (3 mL) and AcOH (1.5 mL) under N2. The mixture is stirred at ambient temperature for 2 h. The reaction is cooled in an ice bath and a slurry of sodium triacetoxyborohydride (0.284 g, 1.34 mmol) and ACN (1.5 mL) is added dropwise. Upon consumption of the starting material by LC/MS, the reaction is concentrated and the residue quenched with saturated NaHCO3 (2×10 mL). The mixture is extracted with DCM (40 mL) and the organics dried over Na2CO3. Evaporation affords [2-benzyloxy-4-(3-benzyloxy-2-cyanobenzyl)-phenylamino]-acetic acid ethyl ester as a green oil: MS (M+H)+=507.

Provenance & Evidence