HCID 22242723, compound → HCID 22242882, compound

HRID 891680Notes

Reaction equation

HRID 891680 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][N:11]([CH3:28])[C:12]([C:14]1[N:15]=[C:16]([N:19]2[CH2:22][CH:21](OS(C)(=O)=O)[CH2:20]2)[S:17][CH:18]=1)=[O:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:29]([O-:32])(=[S:31])[CH3:30].[K+]>CN(C)C=O>[C:29]([S:31][CH:21]1[CH2:20][N:19]([C:16]2[S:17][CH:18]=[C:14]([C:12](=[O:13])[N:11]([CH2:10][CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH3:28])[N:15]=2)[CH2:22]1)(=[O:32])[CH3:30]

Participants

4

Reactant 2

HCID 22242723HCID 22242723, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 22242882HCID 22242882, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-(4-{N-[2-(t-butyldimethylsilyloxy)ethyl]-N-methyl-carbamoyl}-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidine (516 mg, 1.14 mmol) (obtained as described in Reference Example 40(5)) in dimethylformamide (15 ml) was added potassium thioacetate (815 mg, 7.14 mmol) at room temperature. The mixture was stirred in an oil bath (90° C.) for 3 hours. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and 10% 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 hexane:ethyl acetate (1:2) as the eluant to afford 3-acetylthio-1-(4-{N-[2-(t-butyldimethylsilyloxy)ethyl]-N-methyl-carbamoyl}-1,3-thiazol-2-yl)azetidine (279 mg, yield 57%) as a pale brown solid.

Workup

  1. customthe completion of the reaction
  2. customthe reaction mixture was partitioned between ethyl acetate and 10% 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-81116cd4bf0d441aac49f163c8f18f31
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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