HCID 22242713, compound → HCID 22242798, compound

HRID 891601Notes

Reaction equation

HRID 891601 reaction equation
[S:1]1[CH2:6][CH2:5][N:4]([C:7]([C:9]2[N:10]=[C:11]([N:14]3[CH2:17][CH:16](OS(C)(=O)=O)[CH2:15]3)[S:12][CH:13]=2)=[O:8])[CH2:3][CH2:2]1.[C:23]([O-:26])(=[S:25])[CH3:24].[K+]>CN(C)C=O>[C:23]([S:25][CH:16]1[CH2:15][N:14]([C:11]2[S:12][CH:13]=[C:9]([C:7]([N:4]3[CH2:3][CH2:2][S:1][CH2:6][CH2:5]3)=[O:8])[N:10]=2)[CH2:17]1)(=[O:26])[CH3:24]

Participants

4

Reactant 2

HCID 22242713HCID 22242713, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 22242798HCID 22242798, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-(4-thiomorpholinocarbonyl-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidine (709 g, 1.95 mmol) (obtained as described in Reference Example 25(3)) in dimethylformamide (20 ml) was added potassium thioacetate (1.34 g, 11.7 mmol) at room temperature. The mixture was stirred in an oil bath (80° C.) for 5 hours. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium chloride solution. The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and 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 ethyl acetate:n-hexane:methylene chloride (1:1:1) as the eluant to afford 3-acetylthio-1-(4-thiomorpholinocarbonyl-1,3-thiazol-2-yl)azetidine (413 mg, yield 64%) as a pale brown solid.

Workup

  1. customthe completion of the reaction
  2. customthe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium chloride solution
  3. washThe organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and 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-08f6a6f9182d4272b25dfabcec9b5577
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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