Imidazole → HCID 20610887, compound

HRID 1838428Notes

Reaction equation

HRID 1838428 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:9][N:10]([S:16]([C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:21][CH:20]=1)(=[O:18])=[O:17])[CH:11]([CH2:14][OH:15])[CH2:12][OH:13].N1C=CN=C1>CN(C)C=O>[Si:1]([O:13][CH2:12][C@@H:11]([CH2:14][OH:15])[N:10]([CH3:9])[S:16]([C:19]1[CH:20]=[CH:21][C:22]([O:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[CH:23][CH:24]=1)(=[O:18])=[O:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 18753499HCID 18753499, compound

Product 1

HCID 20610887HCID 20610887, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of tert-butyldimethylsilyl chloride (3.53 g, 23.43 mmol) in N,N-dimethylformamide (50 ml) was added dropwise to a solution of N-methyl-N-(4-phenoxybenzenesulfonyl)serinol (8.32 g, 24.66 mmol), which is the product of Example 67(2), and imidazole (4.13 g, 61.65 mmol) in N,N-dimethylformamide (200 ml) at room temperature with stirring. The mixture was further stirred for 2 hours. The solvent of the reaction mixture was evaporated under reduced pressure. To the residue, water was added and this was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using hexane/ethyl acetate=2/1 as the eluant to afford the desired compound (4.15 g, yield 38%) as a colorless oil.

Workup

  1. customat room temperature
  2. stirringThe mixture was further stirred for 2 hours
  3. customThe solvent of the reaction mixture was evaporated under reduced pressure
  4. additionTo the residue, water was added
  5. extractionthis was extracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-2c73755c32d84f45b89f18368a53ad14
Source dataset
uspto-grants-2004_01
Patent number
US06673804B1

Reaction notes

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