6-Acetylamino-3-methoxy-5,6,7,8-tetrahydronaphthalene-2-sulfonyl chloride → N-(6-mercapto-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide

Participants

Reaction Conditions

Reaction Steps

To a suspension of zinc dust (1.16 g; 17.7 mmol) and dimethylsilyl dichloride (2.4 mL; 17.7 mmol) in MeCN (40 mL) was added a solution of 6-acetylamino-3-methoxy-5,6,7,8-tetrahydronaphthalene-2-sulfonyl chloride (1.13 g; 3.55 mmol) in MeCN/DCE (40/10 mL), at room temperature. The reaction suspension was then heated at 81° C. for 4 h, cooled to room temperature, filtered and the solvent evaporated under reduced pressure. The crude residue was purified by reverse-phase semi-prep HPLC eluting with a MeCN—H2O gradient to yield N-(6-mercapto-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide as a white solid and N-[6-(6-acetylamino-3-methoxy-5,6,7,8-tetrahydronaphthalen-2-yldisulfanyl)-7-methoxy-1,2,3,4,-tetrahydronaphthalen-2-yl]acetamide as a tan solid.

Provenance & Evidence