Sodium Hydroxide → (3-{3-[(4-Fluoro-3-methyl-benzyl)-((R)-2-phenyl-propyl)-amino]-propoxy}-phenyl)-acetic Acid

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Reaction Steps

To a solution of {3-[3-((R)-2-Phenyl-propylamino)-propoxy]-phenyl}-acetic acid methyl ester (100 mg, 293 mmol) in methanol (1 ml) was added acetic acid (10% by volume) followed by 4-Fluoro-3-methyl-benzaldehyde (121 mg, 879 mmol) and sodium cyanoborohydride (54.5 mg, 879 mmol). After the resulting mixture was stirred for 18 h at RT water was added to quench the reaction. The solution was made basic by the addition of sodium hydroxide and heated for 30 min. The sample concentrated in vacuo and purified by preparative HPLC (YMC CombiPrep ODS-A, 50×20 mm, 20 mL/min, A: 0.1% trifluoroacetic acid in acetonitrile B: 0.1% aqueous trifluoroacetic acid, A: 10 to 90% during 10 min, UV detection at 254 nm) to give the title compound as a solid (71.6 mg, 54%). MS (ESI) 450.0 (M+H)+.

Provenance & Evidence