Benzaldehyde → HCID 57014776, compound

Participants

Reaction Steps

To a solution of glycine ethyl ester hydrochloride (10.11 g, 72.4 mmol) in 200 mL of dichloromethane was added benzaldehyde (7.36 mL, 72.4 mmol), triethylamine (20.0 mL, 143 mmol), and magnesium sulfate (6 g). The solution was stirred at room temperature for 16 hours, filtered through a glass frit, and concentrated in vacuo. The residue was partitioned between ether and water, and the organic layer was washed with brine. The solution was dried over Na2SO4, filtered, and concentrated in vacuo to provide a pale yellow oil. A portion of this oil (9.90 g, 51.8 mmol) was dissolved in 200 mL of THF and cooled to -78° C. under nitrogen atmosphere. A solution of potassium tert-butoxide in THF (51.8 mL of 1M, 51.8 mmol) was added dropwise to produce a bright red solution. After 20 minutes, a solution of the mesylate from Step F (8.05 g, 54,4 mmol) in 20 mL of THF was added dropwise via cannula, and the solution was allowed to warm to room temperature. After 2 hours, the reaction was poured into EtOAc and washed with sat. NaHCO3 soln. and brine, dried (Na2 SO4), filtered, and concentrated in vacuo to provide the titled product.

Provenance & Evidence