Acetic Anhydride → HCID 21969455、化合物

HRID 2288278ノート

反応式

HRID 2288278 の反応式
[OH:1][CH2:2][C@@H:3]1[C@@H:7]([CH2:8][O:9][Si:10]([C:23]([CH3:26])([CH3:25])[CH3:24])([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:6][C@@H:5]([N:27]2[CH:35]=[C:33]([CH3:34])[C:31](=[O:32])[NH:30][C:28]2=[O:29])[CH2:4]1.[C:36](OC(=O)C)(=[O:38])[CH3:37]>N1C=CC=CC=1.C(Cl)Cl>[Si:10]([O:9][CH2:8][C@H:7]1[O:6][C@@H:5]([N:27]2[CH:35]=[C:33]([CH3:34])[C:31](=[O:32])[NH:30][C:28]2=[O:29])[CH2:4][C@@H:3]1[CH2:2][O:1][C:36](=[O:38])[CH3:37])([C:23]([CH3:26])([CH3:24])[CH3:25])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

参加物

5

反応物 2

HCID 7918Acetic AnhydrideHCID 15334092HCID 15334092、化合物

生成物 1

HCID 21969455HCID 21969455、化合物収率 81.2%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
20 °C

実験手順

Compound 106 (0.5 g, 1.01 mmol) was dissolved in pyridine (10 ml) and acetic anhydride (0.20 ml, 2.12 mmol) was added under an argon atmosphere at room temperature. After being stirred for 24 hours at 20° C., the pyridine was removed in vacuo to give an oil. The oil was diluted with CH2Cl2 (20 ml) and washed with water (20 ml) and saturated NaHCO3 (20 ml). The organic layer was dried over anhydrous MgSO4 and the solvent was evaporated in vacuo to give a white foam. The foam was then purified by flash chromatography in EtOAc/Hexane (6:4) to give 183 (0.44 g, 81%) as a white foam. Tlc (Rf 0.80; EtOAc); 1H NMR (CDCl3): δ8.93 (br, 1 H, NH), 7.69-7.66 (m, 4 H, Ph), 7.48 (d, 1 H, J=1.1 Hz, H-6), 7.46-7.37 (m, 6 H, Ph), 6.17 (dd, 1 H, J=5.7, 6.7 Hz, H-1'), 4.09-4.05 (m, 3 H, H-5' & CH2 -OAc), 3.93-3.91 (m, 1 H, H-5'), 3.79 (dd 1 H, J=11.5, 3.2 Hz, H-5"), 2.80-2.78 (m, 1 H, H-3'), 2.33-2.21 (m, 1 H, H-2'), 2.19-2.16 (m, 1 H, H-2"), 2.03 (s, 3 H, COCH3), 1.62 (s, 3 H, CH3), 1.10 (s, 9 H, C(CH3)3); 13C NMR (CDCl3): δ170.7 (C=O), 163.7 (C4), 150.3 (C2), 135.5-135.2 (d), 133.0, 132.5, 130.1 (C6), 127.9-127.8 (d), 110.9 (C5), 84.7 (C1'), 82.9 (C4'), 64.4 (CH2 -OAc), 64.2 (C5'), 37.3 (C3'), 35.8 (C2'), 26.9, 20.8, 19.4, 12.1; Anal. Calcd for C29H36N2O6Si (536.699): C, 64.90; H, 6.76; N, 5.22. Found: C, 64.57; H 6.79; N, 5.12.

後処理

  1. customthe pyridine was removed in vacuo
  2. customto give an oil
  3. washwashed with water (20 ml) and saturated NaHCO3 (20 ml)
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. customthe solvent was evaporated in vacuo
  6. customto give a white foam
  7. customThe foam was then purified by flash chromatography in EtOAc/Hexane (6:4)

出典と根拠

ORDレコード
ord-5707e8dc0ece45d59e5e2656e510c418
出典データセット
uspto-grants-2000_07
特許番号
US06087482

反応ノート

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