HCID 22243003, compound → HCID 22243010, compound

HRID 891566Notes

Reaction equation

HRID 891566 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[N:11]=[C:12]([N:15]2[CH2:18][CH:17](OS(C)(=O)=O)[CH2:16]2)[S:13][CH:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:24]([O-:27])(=[S:26])[CH3:25].[K+]>CN(C)C=O>[C:24]([S:26][CH:17]1[CH2:16][N:15]([C:12]2[S:13][CH:14]=[C:10]([CH2:9][O:8][Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3])[N:11]=2)[CH2:18]1)(=[O:27])[CH3:25]

Participants

4

Reactant 2

HCID 22243003HCID 22243003, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 22243010HCID 22243010, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-(4-t-butyldimethylsilyloxymethyl-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidine (326.5 mg, 0.86 mmol) (obtained as described in Reference Example 12(3)) in dimethylformamide (16 ml) was added potassium thioacetate (780 mg, 5.41 mmol) at room temperature, and the reaction mixture was then stirred in an oil bath (80° C.) for 2 hours. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The obtained organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using n-hexane:ethyl acetate (4:1) as the eluant to afford 3-acetylthio-1-(4-t-butyldimethylsilyloxymethyl-1,3-thiazol-2-yl)azetidine (191 mg, yield 62%) as a brown syrup.

Workup

  1. customthe completion of the reaction
  2. customthe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
  3. washThe obtained organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium 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-9178daadcc1a4b69885bc1c8e0c39cc4
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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