Lithium hydroxide, monohydrate → (1R,2S)-1-(2-(2-(4-chlorophenyl)-2'-oxospiro[cyclopropane-1,3'-indoline]-1'-yl)ethyl)-1H-imidazole-4-carboxylic acid

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Reaction Steps

To a solution of methyl-1-(2-((1S,2R)-2-(4-chlorophenyl)-2′-oxospiro[cyclopropane-1,3′-indoline]-1′-yl)ethyl)-1H-imidazole-4-carboxylate and methyl-1-(2-((1R,2S)-2-(4-chlorophenyl)-2′-oxospiro[cyclopropane-1,3′-indoline]-1′-yl)ethyl)-1H-imidazole-4-carboxylate (0.07 mmol) in methanol (2 mL) and water (1 mL) was added LiOH.H2O (18 mg, 0.4 mmol) in one portion. The mixture was stirred at room temperature for 3 hours until the starting material was consumed. The mixture was concentrated under reduced pressure and acidified to pH˜3. The residue was dissolved in 2 mL of DMF. Purification by preparative HPLC gave the title compound as a white powder (26 mg, 88%). LC/MS m/e calcd. for C22H18ClN3O3: 407, observed (M+H)+: 408.8 1H NMR (400 MHz, MeOD) δppm 2.10 (dd, J=28.17, 8.46 Hz, 2 H) 3.10 (s, 1 H) 4.31 (s, 2 H) 4.86 (s, 2 H) 6.05 (d, J=7.33 Hz, 1 H) 6.75 (s, 1 H) 6.90-7.45 (m, 6 H) 7.86 (s, 1 H) 8.27 (s, 1 H).

Provenance & Evidence