o-Chlorophenylacetic acid → HCID 117720469, compound

Participants

Reaction Steps

Dissolve 2-(2-chlorophenyl)acetic acid (96.8 mg, 0.56 mmol) and O-(7-aza-1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (200 mg, 0.52 mmol) in dichloromethane (2 mL). Add diisopropylethylamine (183 μL, 1.05 mmol). Stir at ambient temperature for 20 min. Add this reaction mixture to a solution of 4-[(1S,3R)-3-(hydroxymethyl)-1-methyl-1,2,3,4-tetrahydroisoquinolin-5-yl]-2-methyl-butan-2-ol (92 mg, 0.35 mol) in dichloromethane (0.4 mL). Rinse with dichloromethane (1 mL) and stir at ambient temperature for 3.5 hours. Dilute the reaction mixture with water and stir. Extract with dichloromethane and dry the extracts over sodium sulfate, filter, and concentrate under reduced pressure. Purify the residue by silica gel chromatography, eluting with ethyl acetate: hexanes (gradient, 0-60%) to give a residue. Purify the residue by silica gel chromatography, eluting with 10% (2N ammonia in methanol): dichloromethane to give the title compound as a white foam (78 mg, 0.19 mmol). MS (m/z): 416.2 (M+1).

Provenance & Evidence