Triethylamine → 1-(2-t-Butyloxycarbonylaminoethylthio)-3-chloropropan-2-one

Participants

Reaction Steps

To a stirred solution of 1,3-dichloroacetone (5.00 g, 39.37 mmol) in tetrahydrofuran (50 mL) were added 2-t-butyloxycarbonylaminoethanethiol (6.98 g, 37.50 mmol) and triethylamine (3.77 g, 37.50 mmol) at 0° C. After 3 hours the reaction mixture was partitioned between ethyl acetate and water. Organic layer was washed with 1 M hydrochloric acid, water, sodium bicatbonate solution and brine. Organic extract was dried over sodium sulfate and concentrated under reduced pressure to afford oily residue of title product (9.40 g). 1H NMR (CDCl3) δ 1.58 (s, 9H), 2.76 (t, J=6, 2H), 3.40 (m, 2H), 3.58 (s, 2H), 4.42 (s, 2H), 5.00 (br s, 1H).

Provenance & Evidence