O.[OH-].[Li+].[N:4]1([C:8]([C:10]2[N:11]=[CH:12][C:13]([O:16][C:17]3[CH:18]=[C:19]([CH:24]=[C:25]([O:27][C@@H:28]([CH3:34])[CH2:29][O:30][CH:31]([F:33])[F:32])[CH:26]=3)[C:20]([O:22]C)=[O:21])=[N:14][CH:15]=2)=[O:9])[CH2:7][CH2:6][CH2:5]1>O.C1COCC1>[N:4]1([C:8]([C:10]2[N:11]=[CH:12][C:13]([O:16][C:17]3[CH:18]=[C:19]([CH:24]=[C:25]([O:27][C@@H:28]([CH3:34])[CH2:29][O:30][CH:31]([F:32])[F:33])[CH:26]=3)[C:20]([OH:22])=[O:21])=[N:14][CH:15]=2)=[O:9])[CH2:5][CH2:6][CH2:7]1Lithium hydroxide monohydrate (48 mg, 1.13 mmol) in water (5 mL) was added to a solution of methyl 3-{[5-(azetidin-1-ylcarbonyl)pyrazin-2-yl]oxy}-5-({(1S)-2-[(difluoromethyl)oxy]-1-methylethyl}oxy)benzoate (0.33 g, 0.75 mmol) in THF (10 mL) and stirred at RT for 20 hours. The THF was removed in vacuo and the aqueous layer washed with ethyl acetate (50 mL) to remove any impurities. The aqueous layer was acidified and extracted into ethyl acetate (2×50 mL), washed with brine, dried (MgSO4), filtered and the solvent removed in vacuo to give the desired compound as a white foam (0.26 g). m/z 424 (M+H)+
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