HCID 22243065, compound → HCID 22242712, compound

HRID 891742Notes

Reaction equation

HRID 891742 reaction equation
CS(O[CH:6]1[CH2:9][N:8]([C:10]2[S:11][CH:12]=[C:13]([C:15](=[O:33])[NH:16][CH2:17][CH2:18][NH:19][C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=3)=[O:21])[N:14]=2)[CH2:7]1)(=O)=O.[C:34]([O-:37])(=[S:36])[CH3:35].[K+]>CN(C)C=O>[C:34]([S:36][CH:6]1[CH2:9][N:8]([C:10]2[S:11][CH:12]=[C:13]([C:15](=[O:33])[NH:16][CH2:17][CH2:18][NH:19][C:20]([O:22][CH2:23][C:24]3[CH:25]=[CH:26][C:27]([N+:30]([O-:32])=[O:31])=[CH:28][CH:29]=3)=[O:21])[N:14]=2)[CH2:7]1)(=[O:37])[CH3:35]

Participants

4

Reactant 2

HCID 22243065HCID 22243065, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 22242712HCID 22242712, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-methanesulfonyloxy-1-{4-[2-(p-nitrobenzyloxycarbonylamino)-ethylcarbamoyl]-1,3-thiazol-2-yl}azetidine (607.3 mg, 1.22 mmol) (obtained as described in Reference Example 56(6)) in dimethylformamide (33 ml) was added potassium thioacetate (1.06 g, 7.35 mmol) at room temperature. The reaction mixture was stirred in an oil bath (80° C.) for 7 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 successively with 0.5M aqueous hydrochloric acid solution, 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 toluene:acetonitrile (1:2) as the eluant to afford 3-acetylthio-1-{4-[2-(p-nitrobenzyloxycarbonylamino)-ethylcarbamoyl]-1,3-thiazol-2-yl}azetidine (335.8 mg, yield 58%) 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 saturated aqueous sodium hydrogencarbonate solution
  4. washThe organic layer was washed successively with 0.5M aqueous hydrochloric acid solution, 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-65c2d5ee95084daaa2399b6249d099d6
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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