3-(4-Formylbenzoylamino)propionic acid methyl ester → HCID 59518064, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-(4-Formyl-benzoylamino)-propionic acid methyl ester (4.8 g, 20.43 mmol) is dissolved in the anhydrous tetrahydrofuran (THF) (75 mL) and cooled to 0° C. under nitrogen. 2,2-Dimethyl-butyl magnesium bromide (16.3 mL, 1.5M solution in THF, 24.5 mmol) is then added slowly to the solution by addition funnel. The reaction is allowed to stir at 0° C. for 1 hour and the ice bath is removed. The reaction is monitored by TLC or HPLC to determine complete consumption of the aldehyde. The reaction is cooled back down to 0° C. and 1.0N hydrogen chloride solution is dropped in to quench. The solids are dissolved with enough water and the solution is diluted with ether. The two phases are separated and the organic layer is washed with brine, dried over anhydrous sodium sulfate and concentrated. The alcohol (1.6 g, 4.98 mmol) is purified by column chromatography.

Provenance & Evidence