3-Methanesulfonyloxy-1-[4-(3-methoxyazetidine-1-carbonyl)-1,3-oxazol-2-yl]azetidine → 3-Acetylthio-1-[4-(3-methoxyazetidine-1-carbonyl)-1,3-oxazol-2-yl]azetidine

HRID 891815Notes

Reaction equation

HRID 891815 reaction equation
CS(O[CH:6]1[CH2:9][N:8]([C:10]2[O:11][CH:12]=[C:13]([C:15]([N:17]3[CH2:20][CH:19]([O:21][CH3:22])[CH2:18]3)=[O:16])[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[O:11][CH:12]=[C:13]([C:15]([N:17]3[CH2:18][CH:19]([O:21][CH3:22])[CH2:20]3)=[O:16])[N:14]=2)[CH2:9]1)(=[O:26])[CH3:24]

Participants

4

Reactant 2

HCID 222428343-Methanesulfonyloxy-1-[4-(3-methoxyazetidine-1-carbonyl)-1,3-oxazol-2-yl]azetidineHCID 23670855Potassium ethanethioate

Product 1

HCID 222429333-Acetylthio-1-[4-(3-methoxyazetidine-1-carbonyl)-1,3-oxazol-2-yl]azetidineYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-methanesulfonyloxy-1-[4-(3-methoxyazetidine-1-carbonyl)-1,3-oxazol-2-yl]azetidine (580 mg, 1.75 mmol) (obtained as described in Reference Example 73(3)) in dimethylformamide (30 ml) was added potassium thioacetate (1.20 g, 10.5 mmol) at room temperature and the mixture was stirred in an oil bath (80° 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 ethyl acetate→ethyl acetate:methanol (97:3) as the eluant to afford 3-acetylthio-1-[4-(3-methoxyazetidine-1-carbonyl)-1,3-oxazol-2-yl]azetidine (336 mg, yield 62%) as a pale brown solid.

Workup

  1. customthe completion of the reaction
  2. customthe mixture was partitioned between ethyl acetate and 10% aqueous sodium chloride solution
  3. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-be6e9477fbff41258449a6c0ad6acf5f
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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