反应详情

A solution of NaOH (12.6 g, 315 mmol) in H2O (100 mL) was added to a suspension of 6 (50 g, 102 mmol) in MeOH (750 mL) and stirred for 8 h at room temperature. Approximately half of the solvent was removed in vacuo and the remainder was treated dropwise with 1 M aqueous HCl (315 mmol, 315 mL). The white precipitate was filtered, washed with H2O (2×200 mL) and Et2O (3×200 mL) and dried in vacuo to afford a white powder (15, 46.7 g, 100 mmol, 99%) as a mixture of two diastereomers: M.p.: 158-160° C.; 1H-NMR (400 MHz, (CD3)2SO3) δ=11.95 (s, 1H, 1H′), 11.38 (s, 1H, 1H′), 7.85 (d, J=8.0, 1H), 7.77 (d, J=8.0, 1H′), 7.41 (d, J=8.5, 2H), 7.37 (d, J=8.5, 2H′), 6.96 (d, J=8.5, 2H), 6.93 (d, J=8.5, 2H′), 6.04 (s, 1H′), 5.93 (m, 1H, 1H′), 5.90 (s, 1H), 5.64 (d, J=8.0, 1H), 5.63 (d, J=8.0, 1H′), 5.2 (broad, 1H, 1H′), 4.99-4.83 (m, 2H, 2H′), 4.23 (m, 1H), 4.13 (m, 1H′), 3.97 (m, 2H, 2H′), 3.62 (m, 2H, 2H′), 2.20 (m, 2H, 2H′), 1.70 (m, 2H, 2H′, 1.54 (m, 2H, 2H′), 1.41 (m, 2H, 2H′); 13C -NMR (400 MHz, (CD3)2SO3) δ=176.0, 176.0, 164.1, 164.1, 160.6, 160.5, 151.2, 151.2, 143.0, 143.0, 129.3 (2C), 129.3 (2C), 128.9, 128.9, 115.1 (2C), 115.0 (2C), 107.4, 103.4, 102.8, 102.6, 92.2, 91.3, 87.3, 85.1, 84.8, 83.7, 82.6, 80.8, 68.3, 68.3, 62.2, 62.2, 35.1, 35.1, 29.3, 29.3, 26.1, 26.1, 25.4, 25.4; IR (film) ν=3467, 3132, 2938, 1696, 1677, 1245, 1108, 1077, 1046, 1019, 976, 828, 809; HRMS (MALDI-FTMS) m/z 485.1534 (485.1536 calculated for C22H26N2O9Na (M+Na)+).

1. customApproximately half of the solvent was removed in vacuo
2. filtrationThe white precipitate was filtered
3. washwashed with H2O (2×200 mL) and Et2O (3×200 mL)
4. customdried in vacuo
5. customto afford a white powder (15, 46.7 g, 100 mmol, 99%)
6. additionas a mixture of two diastereomers