Imidazole → HCID 68902199, compound

HRID 2099894Notes

Reaction equation

HRID 2099894 reaction equation
[CH3:1][O:2][C:3]1[CH:41]=[CH:40][C:6]([C:7]([O:22][CH2:23][C@:24]23[C@H:30]([OH:31])[C@H:27]([O:28][CH2:29]2)[C@H:26]([N:32]2[CH:39]=[CH:38][C:36](=[O:37])[NH:35][C:33]2=[O:34])[O:25]3)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.N1C=CN=C1.[Si:47](Cl)([C:50]([CH3:53])([CH3:52])[CH3:51])([CH3:49])[CH3:48]>CN(C=O)C.CCOC(C)=O>[Si:47]([O:31][C@@H:30]1[C@@H:27]2[O:28][CH2:29][C@@:24]1([CH2:23][O:22][C:7]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([C:6]1[CH:40]=[CH:41][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)[O:25][C@H:26]2[N:32]1[CH:39]=[CH:38][C:36](=[O:37])[NH:35][C:33]1=[O:34])([C:50]([CH3:53])([CH3:52])[CH3:51])([CH3:49])[CH3:48]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 68902105HCID 68902105, compound

Product 1

HCID 68902199HCID 68902199, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of compound 112 (1.5 g) in anhydrous DMF (10 mL) was stirred with imidazole (0.913 g), trethylamine (375 μL) and t-butyldimethylsilylchloride (0.81 g) for 15 h. The reaction mixture was diluted with EtOAc (40 mL) and washed with aqueous sodium bicarbonate solution (2×20 mL). The organic layer was separated and dried over anhydrous Na2SO4. The solvent was removed and the product purified on silica gel using 10% acetone in CH2Cl2. The appropriate fractions were concentrated and dried to give Compound 114 in 94% yield.

Workup

  1. washwashed with aqueous sodium bicarbonate solution (2×20 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous Na2SO4
  4. customThe solvent was removed
  5. customthe product purified on silica gel using 10% acetone in CH2Cl2
  6. concentrationThe appropriate fractions were concentrated
  7. customdried

Sources & evidence

ORD record
ord-47ecf973f47b4da3825d8a80bbd282b3
Source dataset
uspto-grants-2009_08
Patent number
US07569686B1

Reaction notes

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