Imidazole → HCID 178454081, compound

HRID 1913537Notes

Reaction equation

HRID 1913537 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]1[CH2:13][CH2:12][C@@H:11]([OH:14])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].N1C=CN=C1.[C:21]([Si:25]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)Cl)([CH3:24])([CH3:23])[CH3:22].C(OCC)(=O)C>CN(C)C=O>[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]1[CH2:9][CH2:10][C@@H:11]([O:14][Si:25]([C:21]([CH3:24])([CH3:23])[CH3:22])([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 795Imidazole2×HCID 8857Ethyl AcetateHCID 94078tert-Butyldiphenylchlorosilane2×HCID 178418813HCID 178418813, compound

Product 1

HCID 178454081HCID 178454081, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl(cis-4-hydroxycyclohexyl)carbamate (2.0 g) in dimethylformamide (40 mL), imidazole (756 mg) and t-butyldiphenylchlorosilane (2.86 mL) were added under ice cooling, and the mixture was stirred for 24 hours. Imidazole (226 mg) and t-butyldiphenylchlorosilane (858 μL) were further added thereto, and the mixture was stirred for 6 days. To the reaction solution, ethyl acetate was added, and the organic layer was washed three times with 10% sodium chloride solution, dried over anhydrous sodium sulfate, and filtered. The solvent was distilled off under reduced pressure. This residue was purified by silica gel column chromatography (eluting solvent: hexane/ethyl acetate=98/2-9/1) to obtain the title compound (5.09 g).

Workup

  1. stirringthe mixture was stirred for 6 days
  2. washthe organic layer was washed three times with 10% sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThis residue was purified by silica gel column chromatography (eluting solvent: hexane/ethyl acetate=98/2-9/1)

Sources & evidence

ORD record
ord-0fc36996aa6e4735a88083c9ba81275b
Source dataset
uspto-grants-2013_12
Patent number
US08609710B2

Reaction notes

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