Imidazole → HCID 18689727, compound

HRID 1872009Notes

Reaction equation

HRID 1872009 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH:9][C:10]1[CH:33]=[CH:32][C:13]2[CH:14]([C:24]3[C:25](=[O:31])[NH:26][C:27](=[O:30])[NH:28][CH:29]=3)[C:15]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:16]=3[CH:17]=[CH:18][C:12]=2[CH:11]=1.N1C=CN=C1>CN(C)C=O>[CH3:5][C:4]([Si:1]([CH3:3])([CH3:2])[O:9][C:10]1[CH:33]=[CH:32][C:13]2[CH:14]([C:24]3[C:25](=[O:31])[NH:26][C:27](=[O:30])[NH:28][CH:29]=3)[C:15]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:16]=3[CH:17]=[CH:18][C:12]=2[CH:11]=1)([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 18689766HCID 18689766, compound

Product 1

HCID 18689727HCID 18689727, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Tert-butyl dimethylsilylchloride (0.98 g) was added to a mixture of the product from step (i) and imidazole (0.74 g) in dimethylformamide (20 ml). The reaction mixture was stirred for 3 hours and partitioned between water and ethyl acetate. The organic layer was washed with water, dried (MgSO4) and evaporated under reduced pressure. Purification was by chromatography eluting with 50-70% ethyl acetate in isohexane. Yield 0.71 g.

Workup

  1. custompartitioned between water and ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated under reduced pressure
  5. customPurification
  6. washeluting with 50-70% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-01020e7b6e964910820acbbab9df8abb
Source dataset
uspto-grants-2000_08
Patent number
US06107297

Reaction notes

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