Imidazole → HCID 86585968, compound

HRID 1612519Notes

Reaction equation

HRID 1612519 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[CH2:9][CH2:10][CH2:11][C:12]([N:14]2[CH:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:17][O:16][C:15]2=[O:25])=[O:13])=[CH:4][CH:3]=1.N1C=CN=C1.[Si:32](Cl)([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33].CN(C=[O:44])C>>[Si:32]([O:44][CH:17]1[O:16][C:15](=[O:25])[N:14]([C:12](=[O:13])[CH2:11][CH2:10][CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH:18]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33]

Participants

5

Reactant 4

HCID 795ImidazoleHCID 6228Dimethylformamide2×HCID 28928tert-Butyldimethylsilyl chlorideHCID 121116173-[5-(4-Fluorophenyl)-5-hydroxy-1-oxopentyl]-4-phenyl-2-oxazolidinone

Product 1

HCID 86585968HCID 86585968, compound

Procedure

30 g of 3-[5-(4-Fluorophenyl)-5-hydroxypentanoyl]-4-phenyloxazolidin-2-one are dissolved in 50 ml of DMF. 14.3 g of imidazole and 19 g of tert-butyidimethylsilyl chloride in 25 ml of DMF are added, and the mixture is then stirred at room temperature until the reaction has gone to completion (2–4 h). The reaction solution is concentrated, water is added and the mixture is extracted with ethyl acetate. The organic phase is dried over magnesium sulfate and concentrated, giving 10:

Workup

  1. customhas gone to completion (2–4 h)
  2. concentrationThe reaction solution is concentrated
  3. additionwater is added
  4. extractionthe mixture is extracted with ethyl acetate
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2b1e8bff892f474b8dd85551c3a54e7c
Source dataset
uspto-grants-2006_01
Patent number
US06992067B2

Reaction notes

Loading…