HCID 22242929, compound → HCID 22242754, compound

HRID 891821Notes

Reaction equation

HRID 891821 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 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-methanesulfonyloxy-l-{4-[3-(p-nitrobenzyloxycarbonylamino)azetidine-1-carbonyl]-1,3-thiazol-2-yl}azetidine (390 mg, 0.787 mmol) (obtained as described in Reference Example 75(3)) in dimethylformamide (20 ml) was added potassium thioacetate (539 mg, 4.72 mmol) at room temperature and the mixture was stirred in an oil bath (80° C.) for 10.5 hours. After checking the completion of the reaction, the 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 n-hexane:ethyl acetate (1:3)→ethyl acetate as the eluant to afford 3-acetylthio-1-{4-[3-(p-nitrobenzyloxycarbonylamino)azetidine-1-carbonyl]-1,3-thiazol-2-yl}azetidine (195 mg, yield 52%) as a pale brown solid.

Workup

  1. customat room temperature
  2. customthe completion of the reaction
  3. customthe 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-da0a3a3d35d2482b862b1283fe8fb91a
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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