Imidazole → HCID 21101991, compound

HRID 1353171Notes

Reaction equation

HRID 1353171 reaction equation
[OH:1][CH:2]1[CH2:7][NH:6][C:5](=[O:8])[CH:4]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:3]1.N1C=CN=C1.[C:22]([Si:26]([CH3:29])([CH3:28])Cl)([CH3:25])([CH3:24])[CH3:23]>CN(C=O)C.O>[Si:26]([O:1][CH:2]1[CH2:7][NH:6][C:5](=[O:8])[CH:4]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:15])[CH3:14])[CH2:3]1)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:29])[CH3:28]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 21101990HCID 21101990, compound

Product 1

HCID 21101991HCID 21101991, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of compound 1C (0.355 g, 1.54 mmol) in 5 mL of DMF at room temperature was added imidazole (401 mg, 5.89 mmol) and then t-butyldimethyl chlorosilane (401 mg, 2.31 mmol). After 15 h, the reaction mixture is diluted with 25 mL water and extracted four times with 20 mL portions of ether. The combined organic extracts were washed three times with water, once with saturated NaCl. The organic layer was dried over MgSO4, and then filtered and evaporated under reduced pressure. Purification by silica gel chromatography (2:1 EtOAc/CH2Cl2) provided the title compound (455 mg, 86%) as a white solid. MS [M+H]+: found 345.

Workup

  1. extractionextracted four times with 20 mL portions of ether
  2. washThe combined organic extracts were washed three times with water
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customPurification by silica gel chromatography (2:1 EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-375f860563454e83b912fec110df5f76
Source dataset
uspto-grants-2007_05
Patent number
US07220859B2

Reaction notes

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