P,P-Diphenylphosphinic azide → HCID 11829615, compound

Participants

Reaction Steps

Methyl t-butyl 2-methylidenyl-1,3-dipropionate is reacted with thioacetic acid to form methyl t-butyl 2-acetylthiomethyl-1,3-dipropionate. Methyl t-butyl 2-acetylthiomethyl-1,3-dipropionate is alkylated with potassium carbonate and methyl iodide in the presence of a phase transfer catalyst to form methyl t-butyl 2-acetylthiomethyl-2-methyl-1,3-dipropionate. The t-butyl group is hydrolyzed by acidifying the reaction mixture. The free carboxylic acid group produced by hydrolyzing the t-butyl group is converted to an amino group through a reaction with diphenylphosphoryl azide, thereby forming S-acetyl-2-methylcysteine methyl ester. The acetyl group is removed to form 2-methylcysteine methyl ester.

Provenance & Evidence