Imidazole → HCID 68734484, compound

HRID 1910653Notes

Reaction equation

HRID 1910653 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:21]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[C@@H:20]([OH:32])[C@@H:19]([CH2:33][OH:34])[O:18][C@H:10]1[O:11][CH2:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si:35](Cl)([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36].N1C=CN=C1>CN(C=O)C>[CH2:1]([O:8][C@@H:9]1[C@@H:21]([O:22][CH2:23][C:24]2[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=2)[C@@H:20]([OH:32])[C@@H:19]([CH2:33][O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])[O:18][C@H:10]1[O:11][CH2:12][CH2:13][Si:14]([CH3:16])([CH3:15])[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 68733710HCID 68733710, compound

Product 1

HCID 68734484HCID 68734484, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5.05 (8.90 g, 18 mmol) in DMF (60 mL) was treated with tert-butyldimethylsilyl chloride (6.8 g, 45.2 mmol) and imidazole (3.1 g, 45.2 mmol). After stirring for 8 h, the reaction was concentrated in vacuo. The residue was redissolved in CH2Cl2 then washed with H2O. The organic layer was dried over Na2SO4, decanted, and concentrated in vacuo. The residue was purified by silica gel chromatography (10% EtOAc/petroleum ether) to afford the title compound (10.5 g, 17.4 mmol, 96%). 1H NMR (600 MHz, CDCl3): δ ppm 7.38 (d, J=7.0 Hz, 2H, PhH), 7.33 (t, J=7.6 Hz, 2H, PhH), 7.30-7.26 (m, 3H, PhH, PMPH), 6.85 (d, J=8.2 Hz, 2H, PMPH), 4.92, 4.73 (ABq, J=11.1 Hz, 1H each, OCH2Ph), 4.68, 4.64 (ABq, J=11.4 Hz, 1H each, OCH2PMP), 4.34 (d, J=7.9 Hz, 1H, H-1), 4.04-3.98 (m, 1H, OCHHCH2SiMe3), 3.94 (br s, 1H, H-4), 3.89 (dd, J=10.3, 6.2 Hz, 1H, H-6), 3.82 (dd, J=10.4, 5.7 Hz, 1H, H-6), 3.80 (s, 3H, OMe), 3.64-3.54 (m, 2H, H-2, OCHHCH2SiMe3), 3.45 (dd, J=9.4, 3.2 Hz, 1H, H-3), 3.38 (t, J=6.0 Hz, 1H, H-5), 2.50 (br s, 1H, OH), 1.03 (t, J=8.5 Hz, 2H, OCH2CH2SiMe3), 0.90 (s, 9H, SiCMe3), 0.082, 0.078 (s, 3H each, SiMe2), 0.02 (s, 9H, SiMe3); 13C NMR (125 MHz, CDCl3): δ ppm 159.41, 138.99, 130.26, 129.56, 128.35, 128.14, 127.62, 113.93, 103.33, 80.55, 79.34, 75.23, 74.56, 72.18, 67.24, 66.75, 62.50, 55.33, 25.97, 18.59, 18.41, −1.32, −5.23, −5.28; HRMS calcd for C32H56NO7Si2 [M+NH4]+: 622.3595. found 622.3580.

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. dissolutionThe residue was redissolved in CH2Cl2
  3. washthen washed with H2O
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customdecanted
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel chromatography (10% EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-1fbbc4e2bad344deb303929b9aeb662b
Source dataset
uspto-grants-2013_12
Patent number
US08604004B2

Reaction notes

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