1-(4-Phthalimidomethyl-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidine → 3-Acetylthio-1-(4-phthalimidomethyl-1,3-thiazol-2-yl)azetidine

HRID 891794Notes

Reaction equation

HRID 891794 reaction equation
[C:1]1(=[O:26])[N:5]([CH2:6][C:7]2[N:8]=[C:9]([N:12]3[CH2:15][CH:14](OS(C)(=O)=O)[CH2:13]3)[S:10][CH:11]=2)[C:4](=[O:21])[C:3]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:2]12.[C:27]([O-:30])(=[S:29])[CH3:28].[K+]>CN(C)C=O>[C:27]([S:29][CH:14]1[CH2:15][N:12]([C:9]2[S:10][CH:11]=[C:7]([CH2:6][N:5]3[C:1](=[O:26])[C:2]4=[CH:25][CH:24]=[CH:23][CH:22]=[C:3]4[C:4]3=[O:21])[N:8]=2)[CH2:13]1)(=[O:30])[CH3:28]

Participants

4

Reactant 2

HCID 222430451-(4-Phthalimidomethyl-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidineHCID 23670855Potassium ethanethioate

Product 1

HCID 222430613-Acetylthio-1-(4-phthalimidomethyl-1,3-thiazol-2-yl)azetidineYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-(4-phthalimidomethyl-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidine (726 mg, 1.85 mmol) (obtained as described in Reference Example 68(3)) in dimethylformamide (22 ml) was added potassium thioacetate (1.26 g, 11.1 mmol) at room temperature, and the mixture was stirred in an oil bath (90° C.) for 6.5 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 hexane:ethyl acetate (1:1) as the eluant to afford 3-acetylthio-1-(4-phthalimidomethyl-1,3-thiazol-2-yl)azetidine (599 mg, yield 87%) 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-01d426390c144b68b5c1d7827a6bccd6
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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