L-(+)-Cysteine → HCID 15453674, compound

Participants

Reaction Conditions

Reaction Steps

L-cysteine (15.97 g) was dissolved in a mixture of 1.0 M aqueous sodium hydroxide (265 mL) and 1,4-dioxane (265 mL). 4-Fluorobenzylbromide (24.85 g) was added dropwise over 30 min. After stirring overnight, dioxane was removed and the pH of the residual aqueous solution was adjusted to pH-6 with 3M hydrochloric acid. A white precipitate began to form immediately upon addition of the acid and additional water (150 mL) was added to aid stirring of the thick suspension. The reaction mixture was cooled to 0° C. for 1 h and the precipitates were collected by filtration and washed with cold water, Et2O, and hexane, and dried under high vacuum to give 2(R)-amino-3-(4-fluorobenzylsulfanyl)-propionic acid (28.68 g) as a white solid.

Provenance & Evidence