Ethyl 5-(2-methoxyethoxy)-1-{2-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxy]ethyl}-1H-pyrrolo[2,3-c]pyridine-2-carboxylate → (1R,3S)-5-(2-methoxyethoxy)-1-{2-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxy]ethyl}-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid

Participants

Reaction Steps

60 mg of ethyl 5-(2-methoxyethoxy)-1-{2-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxy]ethyl}-1H-pyrrolo[2,3-c]pyridine-2-carboxylate are dissolved in 2 ml of THF/methanol 3:1, and 0.15 ml of a 1 N lithium hydroxide solution is added. The mixture is stirred at room temperature for 24 h. All volatile components are removed under reduced pressure, the residue is taken up in DMF/acetonitrile, 70 μl of TFA are added and the mixture is filtered and purified by RP-HPLC. This gives 14 mg of (1R,3S)-5-(2-methoxyethoxy)-1-{2-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxy]ethyl}-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid as a colorless oil. C31H37N3O7 (563.66), MS (ESI): 564 (M+H+).

Provenance & Evidence