COC1C=CC(C=[N:10][C@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:12])=CC=1.ClC1C=C(C=CC=1)C(OO)=[O:24].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.Cl.ON>O1CCCC1.C(OCC)(=O)C.O>[C:13]1([C@@H:11]([NH:10][OH:24])[CH3:12])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1
A −78° C. solution of Example 2A (7.15 g, 30 mmole) in tetrahydrofuran (75 mL) was treated with a solution of 3-chloroperoxybenzoic acid (15 g, 60 mmol), warmed to 0 ° C., stirred for 2 hours, diluted with ethyl acetate (100 mL), washed sequentially with 10% (w/w) sodium thiosulfate, saturated sodium bicarbonate, and brine, dried (MgSO4), filtered, and concentrated. The concentrate was dissolved in tetrahydrofuran (100 mL), treated with p-toluene sulfonic acid monohydrate (8.15 g, 42.8 mmol), stirred for 2 hours, treated with a solution of N-hydroxylamine hydrochloride (8.7 g) in water (15 mL), and stirred for 16 hours. The mixture was diluted with ethyl acetate (100 mL), washed with saturated sodium bicarbonate and brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 1:2 ethyl acetate/hexanes to provide 3.53g (86% yield) of the desired product. 1H NMR (300 MHz, CDCl3) δ 7.36-7.20 (m, 5H), 4.09 (q, 1H, J=6.6 Hz), 1.48 (d, 3H, J=6.6 Hz).
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