Hydrochloric Acid → 4-{(1S)-1-[({2,5-dimethyl-4-[4-(trifluoromethyl)benzyl]-3-thienyl}carbonyl)amino]ethyl}benzoic acid

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Reaction Steps

A solution of methyl 4-{(1S)-1-[({2,5-dimethyl-4-[4-(trifluoromethyl)benzyl]-3-thienyl}carbonyl)amino]ethyl}benzoate from Example 11, Step 5 (5.68 g, 11.9 mmol) in THF (305 mL) and MeOH (152 mL) was treated with LiOH (1N in water, 35.8 mL, 35.8 mmol) at r.t. for 44 h and at 50° C. for 3.5 h. The solution was allowed to cool to r.t., and 1N HCl was added (38.2 mL, 3.2 eq). 350 mL of volatiles were removed in vacuo, 800 mL of water was added to the residue and the resulting suspension was stirred for 19 h. The solid was collected by filtration, rinsed with water and dried. The desired product was obtained as a white solid. MS (−APCI): m/z 460 (M−1)−.

Provenance & Evidence