Thioglycolic Acid → HCID 86679547, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-methoxy-3-(methylsulfonyloxy)benzoic acid (prepared in an analogous manner to that described in Scheme 23, Step 2 and 3) (0.362 g, 1.470 mmol) in dry DMF (10.7 ml), HATU (0.559 g, 1.470 mmol) and N-methylmorpholine (0.162 ml, 1.470 mmol) were added. The resulting mixture was stirred at 50° C. under nitrogen until complete conversion of the starting acid into the activated specie (detected by UPLC-MS). Then the solution was allowed to warm to RT and 2-mercaptoacetic acid (0.102 ml, 1.470 mmol) was added drop wise; the resulting mixture was stirred overnight at RT. The solvent was removed under vacuum and the residue was partitioned between EtOAc and HCl 1N; the organic phase was dried over Na2SO4 and the solvent was removed. The crude was purified by preparative HPLC to afford 2-(4-methoxy-3-(methylsulfonyloxy)-benzoylthio)acetic acid (0.152 g, 0.474 mmol, 32.3% yield, MS/ESI+ 342.9 [MNa]+).

Provenance & Evidence