Chloroacetyl chloride → HCID 54439852, compound

Participants

Reaction Conditions

Reaction Steps

A solution of L-aspartic acid dibenzyl ester p-toluene sulfonic acid salt (150 g, 0.309 mol) and distilled triethylamine (93 mL, 0.67 mol) in ethyl acetate (1.1 L) was cooled to 0° C. Chloroacetyl chloride (25.5 mL, 0.32 mol) was added to the resulting solution at a rate such that the reaction temperature did not exceed 10° C. The reaction mixture was then stirred at room temperature for a period of 1.5 hours. The resulting heterogeneous mixture was filtered to remove triethylamine salts. The organic filtrate was sequentially extracted with aqueous 1N HCl (2×250 mL), water (about 300 mL), half-saturated aqueous sodium carbonate (250 mL), water (about 300 mL), and brine (about 300 mL). The organic phase was dried over magnesium sulfate and concentrated in vacuo to provide product 11 (115.6 g, 0.296 mol, 96%) as a viscous brown oil which crystallized on standing. Satisfactory 1H NMR data were obtained for this material. This material was not further purified but was instead used directly in the preparation of iodide 12.

Provenance & Evidence