HCID 22242709, compound → HCID 22242829, compound

HRID 891758Notes

Reaction equation

HRID 891758 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][N:11]([CH:28]([CH3:30])[CH3:29])[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:31]([O-:34])(=[S:33])[CH3:32].[K+]>CN(C)C=O>[C:31]([S:33][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]([CH3:5])([CH3:7])[CH3:6])([CH3:3])[CH3:2])[CH:28]([CH3:30])[CH3:29])[N:15]=2)[CH2:22]1)(=[O:34])[CH3:32]

Participants

4

Reactant 2

HCID 22242709HCID 22242709, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 22242829HCID 22242829, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-(4-{N-[2-(t-butyldimethylsilyloxy)ethyl]-N-isopropyl-carbamoyl}-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidine (649 mg, 1.35 mmol) (obtained as described in Reference Example 59(4)) in dimethylformamide (19 ml) was added potassium thioacetate (930 mg, 8.14 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 (3:1) ethyl acetate as the eluant to afford 3-acetylthio-1-(4-{N-[2-(t-butyldimethylsilyloxy)-ethyl]-N-isopropyl-carbamoyl}-1,3-thiazol-2-yl)azetidine (618 mg, yield 100%) as a pale brown solid.

Workup

  1. customat room temperature
  2. customthe completion of the reaction
  3. customthe reaction mixture was partitioned between ethyl acetate and 10% aqueous sodium chloride solution
  4. washThe organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-67037c70101e416abb6e1438eb7e9993
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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