Imidazole → Methyl 1-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-6-oxo-1,6-dihydropyridine-3-carboxylate

HRID 1878718Notes

Reaction equation

HRID 1878718 reaction equation
[OH:1][CH2:2][C:3]([N:6]1[C:11](=[O:12])[CH:10]=[CH:9][C:8]([C:13]([O:15][CH3:16])=[O:14])=[CH:7]1)([CH3:5])[CH3:4].N1C=CN=C1.Cl[Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]>CN(C=O)C>[Si:23]([O:1][CH2:2][C:3]([N:6]1[C:11](=[O:12])[CH:10]=[CH:9][C:8]([C:13]([O:15][CH3:16])=[O:14])=[CH:7]1)([CH3:5])[CH3:4])([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 68820470Methyl 1-(1-hydroxy-2-methylpropan-2-yl)-6-oxo-1,6-dihydropyridine-3-carboxylate

Product 1

HCID 69234036Methyl 1-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-6-oxo-1,6-dihydropyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 1-(1-hydroxy-2-methylpropan-2-yl)-6-oxo-1,6-dihydropyridine-3-carboxylate (2000 mg, 8.88 mmol), 1H-imidazole (1.51 mg, 22.2 mmol), and chloro-tert-butyldimethylsilane (1405 mg, 9.32 mmol) in DMF (10 mL) was stirred overnight at 23° C. The mixture was partitioned between CH2Cl2 and 5% NaHCO3. The organic was dried over MgSO4 and reduced to an oil under reduced pressure from toluene. MS (ESI pos. ion) m/z (MH+): 340. Calc'd exact mass for C17H29NO4Si: 339.

Workup

  1. customThe mixture was partitioned between CH2Cl2 and 5% NaHCO3
  2. dry with materialThe organic was dried over MgSO4

Sources & evidence

ORD record
ord-3150e05707a943519dd5d5c2372d7479
Source dataset
uspto-grants-2012_11
Patent number
US08314087B2

Reaction notes

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