Imidazole → HCID 86637056, compound

HRID 1096839Notes

Reaction equation

HRID 1096839 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]2[N:23]([CH3:24])[CH:11]([CH2:12][C:13]=1[C:14]1[O:18][N:17]=[C:16]([CH2:19][CH2:20][CH2:21][OH:22])[CH:15]=1)[CH2:10][N:9]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:8]2)=[O:5])[CH3:2].N1C=CN=C1.[CH3:37][C:38]([Si:41](Cl)([CH3:43])[CH3:42])([CH3:40])[CH3:39]>CN(C=O)C.CCOC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[CH:7]2[N:23]([CH3:24])[CH:11]([CH2:12][C:13]=1[C:14]1[O:18][N:17]=[C:16]([CH2:19][CH2:20][CH2:21][O:22][Si:41]([C:38]([CH3:40])([CH3:39])[CH3:37])([CH3:43])[CH3:42])[CH:15]=1)[CH2:10][N:9]([C:25]([O:27][C:28]([CH3:30])([CH3:29])[CH3:31])=[O:26])[CH2:8]2)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 86637057HCID 86637057, compound

Product 1

HCID 86637056HCID 86637056, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of compound B3 (3.56 g, 8.17 mmol), imidazole (1.39 g, 20.4 mmol), and TBDMS-Cl (1.85 g, 12.2 mmol) in DMF (70 mL) was stirred at 0° C. for 30 min, then at rt for 1 h. The mixture was diluted with EtOAc and washed with aq. 10% Na2CO3 (2×), and brine (1×). The org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (EtOAc/heptane 1:6→1:3→1:1) yielded the title compound (2.47 g, 55%). LC-MS: tR=0.94 min; ES+: 550.40.

Workup

  1. waitat rt for 1 h
  2. washwashed with aq. 10% Na2CO3 (2×), and brine (1×)
  3. dry with materialextracts were dried over MgSO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customPurification of the residue by FC (EtOAc/heptane 1:6→1:3→1:1)

Sources & evidence

ORD record
ord-1b5e1787931b4f40b16a0c0091a0a8f6
Source dataset
uspto-grants-2012_03
Patent number
US08138340B2

Reaction notes

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