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

HRID 2115186Notes

Reaction equation

HRID 2115186 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 I (product 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 I (product 1)
  7. customis obtained

Sources & evidence

ORD record
ord-7633d3e866844b62add08276df2edb54
Source dataset
uspto-grants-2008_10
Patent number
US07435727B2

Reaction notes

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