Formaldehyde → HCID 22646456, compound

Participants

Reaction Conditions

Reaction Steps

DL-threo-3-Phenylserine hydrate (5.00 g, 27.6 mmol) and 2N NaOH (13.8 mL, 27.6 mmol) are combined and cooled in an ice-bath. Formaldehyde (2.24 g of a 37% aqueous solution) is added and the reaction mixture is stirred at 0° C. for 21 hours. A solution of 3,4,5-trimethoxybenzoyl chloride (6.36 g, 27.6 mmol) in acetone (20 mL) is added slowly using solid sodium bicarbonate to maintain the pH>7. After stirring for 1 hour the reaction mixture is poured onto water and extracted with ethyl acetate (3×50 mL). The aqueous solution is cooled in an ice-bath, the pH is adjusted to 1 with 1N HCl and the mixture is extracted with methylene chloride (3×100 mL). The combined methylene chloride extracts are washed with water, dried over magnesium sulfate, filtered and concentrated at reduced pressure to afford the desired product as a white solid. CIMS: MH+ 388

Provenance & Evidence