3-Methanesulfonyloxy-1-[4-(methoxycarbonylaminomethyl)-1,3-thiazol-2-yl]azetidine → 3-Acetylthio-1-[4-(methoxycarbonylaminomethyl)-1,3-thiazol-2-yl]azetidine

HRID 891775Notes

Reaction equation

HRID 891775 reaction equation
CS(O[CH:6]1[CH2:9][N:8]([C:10]2[S:11][CH:12]=[C:13]([CH2:15][NH:16][C:17]([O:19][CH3:20])=[O:18])[N:14]=2)[CH2:7]1)(=O)=O.[C:21]([O-:24])(=[S:23])[CH3:22].[K+]>CN(C)C=O>[C:21]([S:23][CH:6]1[CH2:7][N:8]([C:10]2[S:11][CH:12]=[C:13]([CH2:15][NH:16][C:17]([O:19][CH3:20])=[O:18])[N:14]=2)[CH2:9]1)(=[O:24])[CH3:22]

Participants

4

Reactant 2

HCID 222428853-Methanesulfonyloxy-1-[4-(methoxycarbonylaminomethyl)-1,3-thiazol-2-yl]azetidineHCID 23670855Potassium ethanethioate

Product 1

HCID 222428703-Acetylthio-1-[4-(methoxycarbonylaminomethyl)-1,3-thiazol-2-yl]azetidineYield 105.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 3-methanesulfonyloxy-1-[4-(methoxycarbonylamino-methyl)-1,3-thiazol-2-yl]azetidine (448 mg, 1.39 mmol) (obtained as described in Reference Example 63(3)) in dimethylformamide (13 ml) was added potassium thioacetate (952 mg, 8.34 mmol) at room temperature, and the mixture was stirred in an oil bath (90° C.) for 6 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 hexane:ethyl acetate (1:2) as the eluant to afford 3-acetylthio-1-[4-(methoxycarbonylaminomethyl)-1,3-thiazol-2-yl]azetidine (441 mg, yield 100%) 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-f11225a54a6b41339562a6fd1467574f
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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