3-Methanesulfonyloxy-1-(4-succinimidomethyl-1,3-thiazol-2-yl)azetidine → 3-Acetylthio-1-(4-succinimidomethyl-1,3-thiazol-2-yl)azetidine

HRID 891798Notes

Reaction equation

HRID 891798 reaction equation
CS(O[CH:6]1[CH2:9][N:8]([C:10]2[S:11][CH:12]=[C:13]([CH2:15][N:16]3[C:20](=[O:21])[CH2:19][CH2:18][C:17]3=[O:22])[N:14]=2)[CH2:7]1)(=O)=O.[C:23]([O-:26])(=[S:25])[CH3:24].[K+]>CN(C)C=O>[C:23]([S:25][CH:6]1[CH2:7][N:8]([C:10]2[S:11][CH:12]=[C:13]([CH2:15][N:16]3[C:17](=[O:22])[CH2:18][CH2:19][C:20]3=[O:21])[N:14]=2)[CH2:9]1)(=[O:26])[CH3:24]

Participants

4

Reactant 2

HCID 222430693-Methanesulfonyloxy-1-(4-succinimidomethyl-1,3-thiazol-2-yl)azetidineHCID 23670855Potassium ethanethioate

Product 1

HCID 222429253-Acetylthio-1-(4-succinimidomethyl-1,3-thiazol-2-yl)azetidineYield 49.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 3-methanesulfonyloxy-1-(4-succinimidomethyl-1,3-thiazol-2-yl)azetidine (515 mg, 1.49 mmol) (obtained as described in Reference Example 69(3)) in dimethylformamide (15 ml) was added potassium thioacetate (1.02 g, 8.95 mmol) at room temperature, and then stirred in an oil bath (90° C.) for 8 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 ethyl acetate as the eluant to afford 3-acetylthio-1-(4-succinimidomethyl-1,3-thiazol-2-yl)azetidine (238 mg, yield 49%) 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-080f410bbb3e42209b829246d5803163
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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