[Br:1][C:2]1[CH:14]=[CH:13][C:5]2[C:6]([CH2:9][C:10]([OH:12])=O)=[N:7][O:8][C:4]=2[CH:3]=1.CN(C(O[N:23]1N=N[C:25]2C=CC=N[C:24]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[OH:39]N1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>O1CCCC1>[Br:1][C:2]1[CH:14]=[CH:13][C:5]2[C:6]([CH2:9][C:10]([NH:23][CH2:24][CH2:25][OH:39])=[O:12])=[N:7][O:8][C:4]=2[CH:3]=1A suspension of (6-bromo-1,2-benzisoxazol-3-yl)acetic acid (Intermediate 32) (0.10 g) and HATU (0.18 g) in tetrahydrofuran (5 ml) was stirred at room temp. for 10 min then treated with 1-hydroxybenzotriazole (0.05 g) 2-aminoethanol (0.03 ml) and diisopropylethylamine (0.2 ml). The mixture was stirred for a further 18 h then concentrated under vacuum. The residue was partitioned between dichloromethane (5 ml) and 2M aqueous sodium carbonate (5 ml). The organic layer was dried using a hydrophobic filter tube then applied to a Varian Bond-Elut SPE cartridge. Sequential elution with dichloromethane, ether, ethyl acetate, acetonitrile and acetone yieldded the title compound as a white solid (0.08 g).
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