HCID 22242929, compound → HCID 22242754, compound

HRID 891749Notes

Reaction equation

HRID 891749 reaction equation
CS(O[CH:6]1[CH2:9][N:8]([C:10]2[S:11][CH:12]=[C:13]([C:15]([N:17]3[CH2:20][CH:19]([NH:21][C:22]([O:24][CH2:25][C:26]4[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=4)=[O:23])[CH2:18]3)=[O:16])[N:14]=2)[CH2:7]1)(=O)=O.[C:35]([O-:38])(=[S:37])[CH3:36].[K+]>CN(C)C=O>[C:35]([S:37][CH:6]1[CH2:7][N:8]([C:10]2[S:11][CH:12]=[C:13]([C:15]([N:17]3[CH2:18][CH:19]([NH:21][C:22]([O:24][CH2:25][C:26]4[CH:27]=[CH:28][C:29]([N+:32]([O-:34])=[O:33])=[CH:30][CH:31]=4)=[O:23])[CH2:20]3)=[O:16])[N:14]=2)[CH2:9]1)(=[O:38])[CH3:36]

Participants

4

Reactant 2

HCID 22242929HCID 22242929, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 22242754HCID 22242754, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-methanesulfonyloxy-1-{4-[3-(p-nitrobenzyloxycarbonylamino)-azetidine-1-carbonyl]-1,3-thiazol-2-yl}azetidine (760 mg, 1.45 mmol) (obtained as described in Reference Example 57(6)) in dimethylformamide (38 ml) was added potassium thioacetate (993 mg, 8.70 mmol) at room temperature. The mixture was stirred in an oil bath (80° C.) for 9 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 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 as the eluant to afford 3acetylthio-1-{4-[3-(p-nitrobenzyloxycarbonylamino)-azetidine-1-carbonyl]-1,3-thiazol-2-yl}azetidine (397 mg, yield 56%) 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 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-7b32d9978ef7411a9c20cee69ba47845
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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