HCID 22242812, compound → HCID 22242934, compound

HRID 891573Notes

Reaction equation

HRID 891573 reaction equation
CS(O[CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[S:13][CH:14]=[C:15]([C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=3)=[O:18])[N:16]=2)[CH2:8][CH2:7]1)(=O)=O.[C:30]([O-:33])(=[S:32])[CH3:31].[K+]>CN(C)C=O>[C:30]([S:32][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[S:13][CH:14]=[C:15]([C:17]([O:19][CH2:20][C:21]3[CH:22]=[CH:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=3)=[O:18])[N:16]=2)[CH2:8][CH2:7]1)(=[O:33])[CH3:31]

Participants

4

Reactant 2

HCID 22242812HCID 22242812, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 22242934HCID 22242934, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4-methanesulfonyloxy-1-(4-p-nitrobenzyloxycarbonyl-1,3-thiazol-2-yl)piperidine (1.2 g, 2.72 mmol) (obtained as described in Reference Example 14(5)) in dimethylformamide (60 ml) was added potassium thioacetate (625 mg, 5.47 mmol) at room temperature, and the reaction mixture was stirred in an oil bath (90° C.) for 3.5 hours. After checking the completion of the reaction, 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 magnesium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by chromatography on a silica gel column using n-hexane:ethyl acetate (1:1) as the eluant to afford 4-acetylthio-1-(4-p-nitrobenzyloxycarbonyl-1,3-thiazol-2-yl)piperidine (769 mg, yield 88%) 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 hydrogencarbonate solution
  3. washThe 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 obtained residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-ed636c77db9f4c9a9f6406a49d2da30d
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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