Imidazole → HCID 68774133, compound

HRID 1174498Notes

Reaction equation

HRID 1174498 reaction equation
[CH2:1]([C@@H:3]1[CH2:20][C:19]2[CH:18]=[C:17]([O:21]C)[CH:16]=[CH:15][C:14]=2[C@@H:13]2[C@@H:4]1[C@H:5]1[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C:8](=[O:23])[CH2:7][C@H:6]1[CH3:24])[CH3:2].B(F)(F)F.N1C=CN=C1.[Si:34](Cl)([C:37](C)(C)C)([CH3:36])[CH3:35]>ClCCl.CN(C=O)C.CCCCCCC.C(OCC)(=O)C>[CH2:1]([C@@H:3]1[CH2:20][C:19]2[CH:18]=[C:17]([O:21][Si:34]([CH3:37])([CH3:36])[CH3:35])[CH:16]=[CH:15][C:14]=2[C@@H:13]2[C@@H:4]1[C@H:5]1[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C:8](=[O:23])[CH2:7][C@H:6]1[CH3:24])[CH3:2]

Participants

8

Reactant 4

HCID 795ImidazoleHCID 6356Boron trifluorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 59002815HCID 59002815, compound

Product 1

HCID 68774133HCID 68774133, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 21899848Ethylacetate heptaneSolvent

Procedure

To a solution of 4 (270 mg) in dichloromethane (1 ml) was added BF3.DMS complex (800 μl). The mixture was stirred for 1.5 h and then poured into ice-water and extracted with ethyl acetate. The residue thus obtained was triturated with ether/heptane (1/1) to provide 5, (250 mg) as a light rose amorphous solid; Rf 0.27 (heptane/ethyl acetate 8/2). The material was dissolved in DMF (3 ml), imidazole (300 mg) was added followed by t-butyldimethylsilyl chloride. After stirring for 2 h at room temperature the silylation was completed. The reaction was quenched by addition of ice water, followed by extraction of the product with ethyl acetate. Chromatographic purification over a short silica column (heptane/ethyl acetate 9/1) gave 6 (220 mg) as a stiff colourless oil; Rf 0.60 (heptane/ethyl acetate 8/2). NMR (CDCl3) δ 7.12 (1H), 6.62 (1H), 6.18 (1H), 1.03 (s, 3H, 18-CH3), 0.98 (s, 9H, tert.butylsilyl), 0.97, 0.95 (2t, 6H, 7α and 15β ethyl), 0.20 (s, 6H, CH3-silylether).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe residue thus obtained
  3. customwas triturated with ether/heptane (1/1)
  4. customto provide 5, (250 mg) as a light
  5. stirringAfter stirring for 2 h at room temperature the silylation
  6. customThe reaction was quenched by addition of ice water
  7. extractionfollowed by extraction of the product with ethyl acetate
  8. customChromatographic purification over a short silica column (heptane/ethyl acetate 9/1)

Sources & evidence

ORD record
ord-c35b99cff67940219e8f47c43abeca9a
Source dataset
uspto-grants-2010_11
Patent number
US07838516B2

Reaction notes

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