Imidazole → HCID 178501291, compound

HRID 1873592Notes

Reaction equation

HRID 1873592 reaction equation
[OH:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([O:10][CH3:11])=[O:9])[CH2:4][CH2:3]1.[Si:12](Cl)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].N1C=CN=C1>CN(C=O)C>[Si:12]([O:1][C@@H:2]1[CH2:3][CH2:4][C@H:5]([C:8]([O:10][CH3:11])=[O:9])[CH2:6][CH2:7]1)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 178501284HCID 178501284, compound

Product 1

HCID 178501291HCID 178501291, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

99.0 g (0.63 mol) of the compound from Example 51A are dissolved in 2 liters of dry DMF, and 132.0 g (0.88 mol) of tert-butyldimethylsilyl chloride and 80.9 g (1.19 mol) of imidazole are added at RT. The mixture is stirred at RT for 16 h. The solvent is then removed almost to dryness on a rotary evaporator and the residue is taken up in 2 liters of a 1:1 mixture of tert-butyl methyl ether and saturated aqueous sodium bicarbonate solution. The phases are separated, the organic phase is dried over magnesium sulfate and the solvent is removed on a rotary evaporator. The product is used in the next reaction without further purification.

Workup

  1. customThe solvent is then removed almost to dryness on a rotary evaporator
  2. additionthe residue is taken up in 2 liters of a 1:1 mixture of tert-butyl methyl ether and saturated aqueous sodium bicarbonate solution
  3. customThe phases are separated
  4. dry with materialthe organic phase is dried over magnesium sulfate
  5. customthe solvent is removed on a rotary evaporator
  6. customThe product is used in the next reaction without further purification

Sources & evidence

ORD record
ord-f8724b9530bc44658449619dc1088d49
Source dataset
uspto-grants-2012_11
Patent number
US08304412B2

Reaction notes

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