Imidazole → HCID 22730429, compound

HRID 2356117Notes

Reaction equation

HRID 2356117 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][S:5]([C:8]1[S:9][C:10]2[CH:17]=[CH:16][C:15]([C:18]3[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=3)=[CH:14][C:11]=2[C:12]=1[CH3:13])(=[O:7])=[O:6].[Si:28](Cl)([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29].N1C=CN=C1>CN(C=O)C.CCOCC>[Si:28]([O:1][CH2:2][CH2:3][NH:4][S:5]([C:8]1[S:9][C:10]2[CH:17]=[CH:16][C:15]([C:18]3[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=3)=[CH:14][C:11]=2[C:12]=1[CH3:13])(=[O:7])=[O:6])([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 22730062HCID 22730062, compound

Product 1

HCID 22730429HCID 22730429, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of Example 398B (200 mg, 0.5 mmol), tert-butyldimethylsilyl chloride (85 mg, 0.55 mmol) and imidazole (36 mg, 0.6 mmol) in DMF (5 mL) at room temperature was stirred for 24 hours, diluted with ether, filtered through a pad of silica gel, and concentrated to provide the desired product.

Workup

  1. filtrationfiltered through a pad of silica gel
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-873e69825d26437db14c649159cb6be4
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

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