Acetic Anhydride → HCID 21969455, compound

HRID 2288278Notes

Reaction equation

HRID 2288278 reaction equation
[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

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 15334092HCID 15334092, compound

Product 1

HCID 21969455HCID 21969455, compoundYield 81.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-5707e8dc0ece45d59e5e2656e510c418
Source dataset
uspto-grants-2000_07
Patent number
US06087482

Reaction notes

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