Sodium Hydroxide → HCID 11155768, compound

Participants

Reaction Steps

To a stirred solution of 600 mg (1.22 mmol) of (RS,SR)-5-[benzenesulfonyl-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-fluoro-methyl]-[1,2,4]oxadiazole-3-carboxylic acid methyl ester in 5 mL of MeOH/THF 1:1, were added 980 mg (24.5 mmol, 20 eq) of NaOH in solution in 3 mL of water. After 2 hours at RT, aqueous NH4Cl was added until pH=7 was reached, the product was extracted with EtOAc, dried over Na2SO4, filtered and solvent evaporated. Column chromatography on silica gel with CH2Cl2/MeOH 8:2 yielded 300 mg (52%) of (RS,SR)-5-[benzenesulfonyl-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b ]indol-2-yl)-fluoro-methyl]-[1,2,4]oxadiazole-3-carboxylic acid as a white solid, MS: 430 (M-COOH).

Provenance & Evidence