Imidazole → Methyl 2-((tert-butyldimethylsilyloxy)methyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate

HRID 1409427Notes

Reaction equation

HRID 1409427 reaction equation
[OH:1][CH2:2][C:3]1[N:4]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[CH:5]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[N:7]=1.N1C=CN=C1.[CH3:25][C:26]([Si:29](Cl)([CH3:31])[CH3:30])([CH3:28])[CH3:27]>CN(C=O)C.CN(C1C=CN=CC=1)C>[Si:29]([O:1][CH2:2][C:3]1[N:4]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:18])([CH3:17])[CH3:19])[CH:5]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[N:7]=1)([C:26]([CH3:28])([CH3:27])[CH3:25])([CH3:31])[CH3:30]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 70980902Methyl 2-(hydroxymethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate

Product 1

HCID 86714656Methyl 2-((tert-butyldimethylsilyloxy)methyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

Into a flask containing a solution of methyl 2-(hydroxymethyl)-1-((2-(tri-methylsilyl)-ethoxy)methyl)-1H-imidazole-4-carboxylate (1 g, 3.49 mmol) in DMF (25 ml), imidazole (0.490 g, 6.91 mmol), catalytic DMAP and TBDMSCl (0.790 g, 5.27 mmol) were added. The resulting mixture was stirred at RT for 12 h. The reaction mixture was quenched with saturated aqueous solution of NaHCO3 and extracted with EtOAc. The organic layer was concentrated and purified by flash column chromatography. Yield 800 mg. 1H-NMR (400 MHz; DMSO-d6): δ −0.04 (s, 9H), 0.05 (s, 6H), 0.80 (t, 2H), 0.86 (s, 9H), 3.49 (t, 2H), 3.74 (s, 3H), 4.71 (s, 2H), 5.41 (s, 2H), 8.02 (s, 1H). LC-MS: [M+1]=401.10.

Workup

  1. additionwere added
  2. customThe reaction mixture was quenched with saturated aqueous solution of NaHCO3
  3. extractionextracted with EtOAc
  4. concentrationThe organic layer was concentrated
  5. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-9919a944f3e547e5bfc24add61a3cf18
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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