CC(O)C.[NH2:5][C:6]1[N:11]=[CH:10][N:9]=[C:8]([N:12]2[CH2:17][CH2:16][CH:15]([C:18]([OH:20])=[O:19])[C@@H:14]([NH:21][C@H](C3C=CC=CC=3)C)[CH2:13]2)[C:7]=1[F:30].O.[F-].[K+].[H][H]>[OH-].[OH-].[Pd+2].O>[NH2:21][C@@H:14]1[CH:15]([C:18]([OH:20])=[O:19])[CH2:16][CH2:17][N:12]([C:8]2[C:7]([F:30])=[C:6]([NH2:5])[N:11]=[CH:10][N:9]=2)[CH2:13]1To a 10 L reaction were charged under N2, i-PrOH (3.5 L), H2O (3.5 L), 3-7 (1.0 equiv, 0.97 mol, 350 g), potassium fluoride mono hydrate (290 g, 3.0 eq, 3.0 mol) and 35 g of 20% Pd(OH)2/C (10% v/w). After evacuated/refilled with hydrogen three times, the mixture was warmed to 40-50° C. and vigorously stirred at that temperature under 1 atmosphere of hydrogen. After 18 hours, LC/MS indicated <1% of starting material 3-7 remained. The mixture was purged with N2 for 20 min, cooled to 22° C., and filtered. Both the wet cake and filtrate contained the product and processed separately.
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