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Step B: Methyl 2-((N-(2-methoxy-2-oxoethyl)-4-methylphenylsulfonamido)methyl)-4-nitrobenzoate: Methyl 2-(4-methylphenylsulfonamido)acetate (4.314 g, 17.73 mmol) was dissolved in 50 mL DMF at ambient temperature under N2. Sodium hydride (0.8669 g, 21.67 mmol) was added and the mixture stirred for 2 hours. To the solution was added a 50 mL DMF solution containing <strong>[133446-99-8]methyl <strong>[133446-99-8]2-(bromomethyl)-4-nitrobenzoate</strong></strong> (5.4 g, 19.70 mmol). The solution was stirred at ambient temperature for 12 hours. The reaction was quenched by adding 10% HCl, and the mixture diluted with copious amounts of water. The aqueous layer was extracted with ether, and the combined organic layers were dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography using 10-30% EtOAc/hexanes to provide the desired product.
Methyl 2-(chloromethyl)-4-phenoxybenzoate (0.68 g, 2.46 mmol),N-p-toluenesulfonylglycine methyl ester (0.7 g, 2.88 mmol), potassium carbonate (0.68 g, 4.923 mmol), potassium iodide (0.16 g, 0.96 mmol), DMF was added to the reaction flask, replaced with nitrogen, and heated to 50 C. After reacting for 1 hour, 2 mL of methanolic sodium methoxide solution was added to room temperature and stirred for 30 min. After the reaction was completed by thin layer chromatography, 40 mL of purified water was added to the reaction mixture, and glacial acetic acid was added dropwise with stirring to adjust pH=7, suction filtration, and the filter cake was added with acetone. 4 mL was stirred for 2 hours, and suction filtered to give the title compound 2d (525 mg, 72.5%).
102361 A reactor was charged with a solution of 2-chloromethyl-4-phenoxybenzoic acid methyl ester (68 Kg) in DMF, and stirring was initiated. The reactor was then charged with p-toluenesulfonylglycine methyl ester (66 Kg), potassium carbonate (60 Kg), and sodium iodide (4 Kg). The mixture was heated to at least 50 C until reaction completion. The mixture was cooled. Sodium methoxide in methanol was charged and the mixture was stirred until reaction completion. Acetic acid and water were added, and themixture was stirred, filtered and washed with water. Solid was purified by acetone trituration and dried inan oven giving 3a (Yield from step b): 58%; HPLC: 99.4%). ?H NMR (200 MHz, DMSO-d6) d 11.60 (s,1 H), 8.74 (s, 1H), 8.32 (d, J = 9.0 Hz, 1 H), 7.60 (dd, J = 2.3 & 9.0 Hz, 1H), 7.49 (m, 3 H), 7.24 (m, 3 H),3.96 (s, 3 H); MS-(+)-ion M+1 = 296.09
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