Hydrochloric Acid → HCID 70363655, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3.25 g (10.0 mmole) N-phthaloyl-0-methyl-(S)-tyrosine in 50 ml 1,2-dichloroethane was combined with 2.29 g (11.0 mmole) phosphorus pentachloride at 0° C. and agitated at first for 30 minutes at 0° C. and then for 16 hours at room temperature. After the addition of another 50 ml 1,2-dichloroethane, a tenth of the solution was rapidly added to an agitated solution of 1.38 g (10.0 mmole) catechol dimethylether and 160 mg iron-(III)-chloride (10 mole percent) in 70 ml 1,2-dichloroethane. The reaction mixture was heated to 50° C. and the remaining solution of acid chloride was added dropwise in a continuous manner over 12 hours. The mixture was agitated 12 hours further at 50° C. and then cooled down to 0° C. 100 ml 1N hydrochloric acid cooled down to 0° C. were added and the mixture was agitated for 24 hours at room temperature. The aqueous phase was separated off and extracted twice with 40 ml methylene chloride per extraction. The combined organic phases were washed with 150 ml saturated, aqueous sodium hydrogen carbonate solution, then with 100 ml water, and dried over sodium sulfate. After removal of the solvent at 40° C. under reduced pressure, the raw product was chromatographed over a silica gel column. 1.93 g (43 % of theory) (S)-3,4-dimethoxyphenyl-[2-(4-methoxyphenyl)-1-phthalimidoethyl]-ketone of reagent purity were obtained as oil.

Provenance & Evidence