Imidazole → HCID 22242901, compound

HRID 891628Notes

Reaction equation

HRID 891628 reaction equation
[OH:1][CH:2]1[CH2:5][N:4]([C:6]2[S:7][CH:8]=[C:9]([C:11](=[O:16])[NH:12][CH2:13][CH2:14][OH:15])[N:10]=2)[CH2:3]1.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18].N1C=CN=C1.CO>CN(C)C=O>[Si:17]([O:15][CH2:14][CH2:13][NH:12][C:11]([C:9]1[N:10]=[C:6]([N:4]2[CH2:5][CH:2]([OH:1])[CH2:3]2)[S:7][CH:8]=1)=[O:16])([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 887MethanolHCID 28928tert-Butyldimethylsilyl chlorideHCID 69544027HCID 69544027, compound

Product 1

HCID 22242901HCID 22242901, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-hydroxy-1-(4-hydroxyethylcarbamoyl-1,3-thiazol-2-yl)azetidine (481.2 mg, 1.98 mmol) (obtained as described in Reference Example 33(3)) in dimethylformamide (24.0 ml) were added t-butyldimethylsilyl chloride (352 mg, 2.3 mmol) and imidazole (116.3 mg, 2.4 mmol) in an ice bath, and the mixture was stirred in the ice bath for 4 hours. After checking the completion of the reaction, methanol was added thereto and the reaction mixture was stirred for 30 minutes. The reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using hexane:ethyl acetate (2:3) as the eluant to afford 1-{4-[2-(t-butyldimethylsilyloxy)-ethylcarbamoyl]-1,3-thiazol-2-yl}-3-hydroxyazetidine (531.1 mg, yield 75%) as a colorless and transparent syrup.

Workup

  1. additionwas added
  2. customThe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
  3. washThe organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-e87e7bd452fd403686fd61bfc453977e
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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