反应详情

A solution of 2N aqueous NaOH (2.0 mL, 4.0 mmol) is added to a solution of the title compound of Example 40, [2-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-acetic acid methyl ester (57 mg, 0.20 mmol) in MeOH (2.0 mL). The reaction is stirred for 3 h, then neutralized by addition of 2N aqueous HCl (2.0 mL). The mixture is concentrated on a Savant Speedvac to give a yellow solid. The solid is triturated with EtOAc, filtered and the filtrate is evaporated to give a yellow solid. This is dissolved in 2 mL water loaded onto a preparative reverse phase HPLC column (YMC CombiPrep Pro C18, 50×20 mm I.D., particle size S-5 micron, 12 nM) and eluted at 30 mL/min with a gradient of 90:10 (0.1% TFA in water:MeCN) to 10:90 over 5 min. Then held at 10:90 until 7 min. Fractions containing product are combined and concentrated on a Savant Speedvac to yield [2-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-acetic acid as a white solid: [M−1]−=269.

1. concentrationThe mixture is concentrated on a Savant Speedvac
2. customto give a yellow solid
3. customThe solid is triturated with EtOAc
4. filtrationfiltered
5. customthe filtrate is evaporated
6. customto give a yellow solid
7. washeluted at 30 mL/min with a gradient of 90:10 (0.1% TFA in water:MeCN) to 10:90 over 5 min
8. waitThen held at 10:90 until 7 min
9. additionFractions containing product
10. concentrationconcentrated on a Savant Speedvac