Imidazole → 3-[5-(tert-Butyl-dimethyl-silanyloxy)-5-phenyl-pentanoyl]-4-phenyl-oxazolidin-2-on

HRID 506838Notes

Reaction equation

HRID 506838 reaction equation
[OH:1][CH:2]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:3][CH2:4][CH2:5][C:6]([N:8]1[CH:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:11][O:10][C:9]1=[O:19])=[O:7].N1C=CN=C1.[C:31]([Si:35](Cl)([CH3:37])[CH3:36])([CH3:34])([CH3:33])[CH3:32]>CN(C=O)C>[C:31]([Si:35]([CH3:37])([CH3:36])[O:1][CH:2]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:3][CH2:4][CH2:5][C:6]([N:8]1[CH:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:11][O:10][C:9]1=[O:19])=[O:7])([CH3:34])([CH3:33])[CH3:32]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 183745813-(5-Hydroxy-5-phenylpentanoyl)-4-phenyl-1,3-oxazolidin-2-one

Product 1

HCID 210831813-[5-(tert-Butyl-dimethyl-silanyloxy)-5-phenyl-pentanoyl]-4-phenyl-oxazolidin-2-on

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

30 g of 3-(5-Hydroxy-5-phenyl-pentanoyl)-4-phenyl-oxazolidin-2-on are solved in 50 ml of DMF. After addition of 14.3 g of imidazol and 19 g of tert.-Butyl-dimethylsilylchlorid in 25 ml of DMF the reaction is stirred at room temperature until all components are dissolved (2-4 h). The reaction solution is evaporated, and after water was added extracted by acetic acid ethylester. After drying of the organic phase by magnesium sulfate and evaporation compound 1 is obtained: C26H35NO4Si (453.6) MS (ESI+) 476 (M+Na+).

Workup

  1. dissolutionare dissolved (2-4 h)
  2. customThe reaction solution is evaporated
  3. additionafter water was added
  4. extractionextracted by acetic acid ethylester
  5. dry with materialAfter drying of the organic phase by magnesium sulfate
  6. customevaporation compound 1
  7. customis obtained

Sources & evidence

ORD record
ord-780b71dc97854c4fafc314e6142bc6d6
Source dataset
uspto-grants-2010_08
Patent number
US07786103B2

Reaction notes

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