CC[C@@H]1[C@@H]2C[C@H]([C@@H](OC3C4C(=CC=CC=4)C(O[C@@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C([O:22]C)C=C4)N(CC2)C1.C([C:62]1[CH:63]=[C:64]([F:69])[C:65]([Cl:68])=[N:66][CH:67]=1)C=C.S([O-])([O-])=O.[Na+].[Na+].[C:76]([OH:80])(C)([CH3:78])[CH3:77]>O>[Cl:68][C:65]1[N:66]=[CH:67][C:62]([CH2:77][C@@H:76]([OH:80])[CH2:78][OH:22])=[CH:63][C:64]=1[F:69]AD-mix-beta (45 g) was added portion wise to a solution of 2 (4.5 g, 26.2 mmol) in t-butanol (135 mL) and H2O (135 mL) at 5° C. The mixture was stirred at room temperature for 16 hrs, and then cooled to 5° C. and treated with excess sodium sulfite for 20 min. The mixture was diluted with water (100 mL) and extracted with ethyl acetate (100 mL×2). The combined organic layers were washed with brine, dried over sodium sulfate, concentrated, and chromatographed on silica gel eluted with 67% ethyl acetate in hexanes and ethyl acetate to afford 5.0 g (92%) of 3 as a colorless oil. 1HNMR (CDCl3) δ 2.04 (2 H, brs), 2.81 (2 H, m), 3.54 (1 H, t, J=5.0 Hz), 3.75 (1 H d, J=11.0 Hz), 3.94 (1 H, m), 7.46 (1 H, d, J=9.0 Hz), 8.10 (1 H, s); LC/MS (M+1) 207.
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