Hydrochloric Acid → HCID 68543218, compound

Participants

Reaction Steps

Steps B-C: 7-chloro-3-trifluoromethanesulfonyloxy-benzo[b]thiophene-2-carboxylic acid methyl ester (104 mg, 0.28 mmol) in DMF (2 ml) was added to a mixture of sodium tert-butoxide (54 mg, 0.56 mmol) and methyl thioglycolate dissolved in DMF (1 ml). After 16 hr, water was added and the mixture was neutralized with 1N HCl. It was then extracted with EtOAc, dried over MgSO4, filtered, and the solvent was removed in vacuo. An inseparable mixture of hydrolized starting material/desired product with a 1:1.6 ratio resulted. This mixture was then treated with ethyl bromoacetate (120 μl, 1.1 mmol) in the presence of K2CO3 (90 mg, 0.65 mmol) at 60° C. After 24 hr, water was added and the mixture was extracted with EtOAc. Removal of solvent and purification by reverse phase HPLC yielded 19 mg (16% over 2 steps) of 7-chloro-1-ethoxycarbonylmethoxy-3,8-dithia-cyclopenta[a]indene-2-carboxylic acid methyl ester. HRMS (ESI-, m/z) calcd for [M-H]1−, 340.93506, found, 340.9345.

Provenance & Evidence