[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([OH:12])=O.C1C=[C:17]2[N:19]=NN(O)[C:16]2=[CH:15]C=1.O.CCN=C=NCCCN(C)C.Cl.N1CCC1>C(Cl)Cl>[N:19]1([C:10](=[O:12])[CH2:9][C:3]2[CH:4]=[CH:5][C:6]([OH:8])=[CH:7][C:2]=2[F:1])[CH2:17][CH2:16][CH2:15]12-(2-fluoro-4-hydroxyphenyl)acetic acid (1 g, 5.88 mmol), HOBT monohydrate (2.7 g, 17.6 mmol), and EDC.HCl (3.38 g, 17.6 mmol) were dissolved in 25 mL of DCM and stirred at rt for 30 min. Azetidine (1 g, 17.6 mmol) was added to this mixture and the reaction aged at rt for 3 hrs. The mixture was concentrated under reduced pressure and the residue purified by column chromatography on silica gel (KP-Sil 50 g SNAP column, Biotage system) eluting with 100% EtOAc over 14 CV to give the desired product. LC/MS (m/z): 210 (M+H)+.
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