Oxalyl chloride → HCID 86634494, compound

Participants

Reaction Steps

Treat a solution of 6-{1-[4-(3,3-dimethyl-2-oxobutoxy)-3-methylphenyl]-1-ethylpropyl}naphthalene-2-carboxylic acid (0.11 g, 0.246 mmol) in CH2CL2 (1.0 mL) dropwise with oxalyl chloride (0.13 mL, 1.48 mmol). Stir the solution at RT for 1 h and concentrate to give 6-{1-[4-(3,3-dimethyl-2-oxobutoxy)-3-methylphenyl]-1-ethylpropyl}naphthalene-2-carbonyl chloride (“the acid chloride”). Treat a mixture of methylglycine HCl (0.031 g, 0.25 mmol) and Et3N (0.51 mL, 0.37 mmol) in CH2CL2 (3 mL) with a solution of the acid chloride (0.057 g, 0.123 mmol) in CH2CL2 (1 mL). Stir the reaction at RT for 16 h and concentrate. Dissolve the residue in THF (0.5 mL) and MeOH (1.0 mL) and treat with 2N NaOH (0.24 mL, 0.48 mmol). Heat the solution to 50° C. for 16 h, concentrate, dilute with CH2CL2 and water (10 mL each). Acidify the resulting mixture to pH 1 using 5N HCl. Wash the organic layer with brine, dry over Na2SO4, and filter. Concentrate the filtrate and purify by silica gel radial chromatography (10:90 MeOH:CH2CL2) to give the title compound as a white solid (0.021 g, 34%). MS (ES) m/e 504 (M+1).

Provenance & Evidence