Sodium Hydroxide → (RS,SR)-2-benzenesulfonyl-2-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-propionic acid

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Reaction Conditions

Reaction Steps

To 50 mg (0.115 mmol) of (RS,SR)-2-benzenesulfonyl-2-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-propionic acid methyl ester (example 3) in 4 mL of THF/MeOH 1:1, 0.29 mL of 2M NaOH (0.58 mmol, 5 eq) were added. The reaction mixture was stirred at 60° C. for 3 hours, acidified to pH=6 with aqueous NH4Cl and extracted with EtOAc. The combined organic phases were dried over Na2SO4, filtered and evaporated. Column chromatography on silica gel with CH2Cl2/MeOH 3:1 yielded 40 mg (82%) of (RS,SR)-2-benzenesulfonyl-2-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-propionic acid as a white solid, MS: 435 (MNH4+).

Provenance & Evidence