Triethylamine → N-(2-Chloro-6-fluorobenzyl)-3-{3-[(2R)-2-({(2R)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)propyl]phenyl}propanamide

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A solution of 3-{3-[(2R)-2-({(2R)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)propyl]phenyl}propanoic acid (Preparation 60) (150 mg, 0.29 mmol), O-(1H-benzotrizol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (133 mg, 0.35 mmol), 2-fluoro-6-chlorobenzylamine (56 mg, 0.35 mmol) and triethylamine (0.12 ml, 0.88 mmol) were stirred at room temperature for 16 hours in N,N-dimethylformamide (3 ml). The solvent was removed in vacuo and the resulting brown oil was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (98:2:0.2 followed by 94:6:0.6 by volume) to give the title compound as a white foam (30 mg).

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