p-Toluenesulfonic acid → 6-[Cyclopropyl-(2,3-dichlorobenzyl)carbamoyl]-7-[2-(2-hydroxy-ethoxy)thiazol-5-yl]-3,9-diazabicyclo[3.3.1]non-6-ene-3,9-dicarboxylic acid di-tert-butyl ester

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Reaction Steps

A sol. of compound E8 (0.37 mmol; 0.31 g) in MeOH (3.75 mL) was treated with para-toluenesulfonic acid (0.41 mmol; 78 mg), and the mixture was stirred at rt for 30 min. 10% aq. Na2CO3 (3.0 mL) was added and the solvents were partially removed under reduced pressure. The resulting suspension was extracted with EtOAc (25 mL), washed with 10% aq. Na2CO3 (25 mL), sat. aq. NaHCO3 (25 mL), and brine (25 mL). The org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. The product (0.26 g; 99%) was used for the next step without purification. LC-MS: tR=1.10 min; ES+: 709.41.

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