Imidazole → HCID 131727561, compound

HRID 2099891Notes

Reaction equation

HRID 2099891 reaction equation
N1C=CN=C1.[OH:6][CH2:7][C@@:8]12[C@H:14]([O:15][CH2:16][C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=[CH:19][CH:18]=3)[C@H:11]([O:12][CH2:13]1)[C@H:10]([N:27]1[CH:34]=[CH:33][C:31](=[O:32])[NH:30][C:28]1=[O:29])[O:9]2.[Si:35](Cl)([C:48]([CH3:51])([CH3:50])[CH3:49])([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>CN(C=O)C.CCOC(C)=O>[Si:35]([O:6][CH2:7][C@:8]12[C@H:14]([O:15][CH2:16][C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=[CH:19][CH:18]=3)[C@H:11]([O:12][CH2:13]1)[C@H:10]([N:27]1[CH:34]=[CH:33][C:31](=[O:32])[NH:30][C:28]1=[O:29])[O:9]2)([C:48]([CH3:51])([CH3:50])[CH3:49])([C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 131727562HCID 131727562, compound

Product 1

HCID 131727561HCID 131727561, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Imidazole (5.5 g) was added to Compound 108 (8.83 g) dissolved in anhydrous DMF (100 mL) followed by addition of t-butyldiphenylsilylchloride (8.5 mL). The reaction mixture was stirred for 15 h at room temperature when it was complete. The reaction mixture was diluted with EtOAc (400 mL) and washed with saturated sodium bicarbonate solution (3×500 mL) followed by water (2×200 mL). The organic layer was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. Finally the residue was purified on a silica gel column using 30% EtOAc in CH2Cl2 as the eluant. Appropriate fractions were collected and concentrated to give Compound 109 in 78% yield.

Workup

  1. washwashed with saturated sodium bicarbonate solution (3×500 mL)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customFinally the residue was purified on a silica gel column
  5. customAppropriate fractions were collected
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-48300c30fdb6403780fd3a8ac4a1d9cf
Source dataset
uspto-grants-2009_08
Patent number
US07569686B1

Reaction notes

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