反应详情

A solution of methyl (2S)-2-[(benzyloxy)carbonyl]amino-3-[3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanoate (6.90 g, 15.2 mmol), sodium periodate (16.3 g, 76.1 mmol), tetrahydrofuran (156 mL), ammonium acetate (4.69 g, 60.9 mmol) and water (156 mL) was stirred at 25° C. for 24 h. The reaction was diluted with ethyl acetate and 1 N HCl solution. The aqueous solution was extracted with ethyl acetate once. The combined organic solutions were washed with brine, dried with sodium sulfate, filtered, and concentrated in vacuo. The crude residue was crystallized in ethyl acetate to yield the desired product (5.65 g, 80%). 1H NMR (400 MHz, CD3OD): δ 7.3 (m, 5H), 7.16 (d, 1H), 7.0 (m, 2H), 5.02 (m, 2H), 4.42 (m, 1H), 3.68 (s, 3H), 3.10 (m, 1H), 2.88 (m, 1H), 2.28 (s, 3H); MF=C19H22BNO6; LCMS found for C19H23BNO6 (M+H)+: m/z=372.

1. extractionThe aqueous solution was extracted with ethyl acetate once
2. washThe combined organic solutions were washed with brine
3. dry with materialdried with sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customThe crude residue was crystallized in ethyl acetate