Imidazole → HCID 131719596, compound

HRID 864505Notes

Reaction equation

HRID 864505 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:10][C@H:9]3[C@@H:11]([OH:18])[C@H:12]([OH:17])[C@@H:13]([CH2:15][OH:16])[O:14][C@H:8]3[N:7]([CH2:19][CH:20]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[CH3:21])[C:6]=2[CH:27]=1.N1C=CN=C1.[Si:33](Cl)([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34].C(Cl)(Cl)Cl>CN(C)C=O.C(OCC)(=O)C.CO>[Si:33]([O:16][CH2:15][C@H:13]1[O:14][C@@H:8]2[C@@H:9]([S:10][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:27][C:6]=3[N:7]2[CH2:19][CH:20]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[CH3:21])[C@@H:11]([OH:18])[C@@H:12]1[OH:17])([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 6212ChloroformHCID 28928tert-Butyldimethylsilyl chlorideHCID 131719597HCID 131719597, compound

Product 1

HCID 131719596HCID 131719596, compoundYield 9.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21584119Ethylacetate methanolSolvent

Procedure

To the solution of 1.51 g of the compound (10) obtained in Example 10 and 0.48 g of imidazole in 3.5 ml of dimethylformamide, 0.55 g of tert-butyldimethylsilyl chloride was added dropwise, and the mixture was stirred for 23 hours at room temperature. Chloroform was added to the reaction solution, and the mixture was washed with water. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography, and 180 mg (yield: 9.4%) of the title compound was obtained from the fraction of ethyl acetate-methanol (19:1).

Workup

  1. washthe mixture was washed with water
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-518e4cd615a04c92b85913c15d491f32
Source dataset
uspto-grants-1996_10
Patent number
US05563137

Reaction notes

Loading…