Benzoic Acid → HCID 67597759, compound

Participants

Reaction Steps

Prepared according to the method described in Example 27 from (3S)-1-(3'-chlorobiphenyl-4-yl)-5-(3-pyridyl)-3-pentanol (0.137 g, Example 86), benzoic acid (0.061 g), triphenylphosphine (0.131 g) and diethyl azodicarboxylate (0.061 ml). The mixture was concentrated under reduced pressure and the residue redissolved in methanol (8 ml) and water (2 ml). Solid sodium hydroxide (0.2 g) was added and the reaction stirred for 2 hours before being poured into a solution of saturated aqueous sodium hydrogen carbonate. The mixture was extracted with ethyl acetate, the combined organic extracts dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give an oil which was converted to the oxalate salt upon treatment with oxalic acid in ether (excess) to give the title compound as a solid (0.033 g).

Provenance & Evidence