107922-46-3

Methyl 3-aminobenzoate (10 g, 66.2 mmol) was dissolved in pyridine (100 mL) and cooled in an ice bath for 15 minutes. Benzenesulfonyl chloride (8.53 mL, 66.2 mmol) was added slowly dropwise over 5 min using a syringe, followed by stirring the reaction mixture and gradually warming it to room temperature, the reaction lasted for 16 hours. The reaction mixture was slowly poured into a 1 M HCl solution (250 mL total volume) containing ice and the pH was adjusted to 2-3 to form a heterogeneous acidic mixture. The precipitate was collected by filtration and washed with plenty of water. The resulting solid was dried under high vacuum for 12 h to give the target product methyl 3-benzenesulfonylaminobenzoate (19.3 g, 100% yield) as an off-white solid.

[1] Patent: WO2010/126922, 2010, A1. Location in patent: Page/Page column 26
[2] Journal of Medicinal Chemistry, 2009, vol. 52, # 10, p. 3317 - 3327
[3] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 15, p. 4436 - 4440