HCID 22242902, compound → HCID 22242786, compound

HRID 891618Notes

Reaction equation

HRID 891618 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]([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[S: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 22242902HCID 22242902, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 22242786HCID 22242786, compoundYield 68%

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-thiazol-2-yl]azetidine (560 mg, 1.61 mmol) (obtained as described in Reference Example 31(4)) in dimethylformamide (28 ml) was added potassium thioacetate (1.10 g, 9.67 mmol) at room temperature. The mixture was stirred in an oil bath (80° C.) for 4.5 hours. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and 10% aqueous sodium chloride solution. The organic layer was washed successively 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-methoxy-azetidine-1-carbonyl)-1,3-thiazol-2-yl]azetidine (356 mg, yield 68%) as a pale brown solid.

Workup

  1. customat room temperature
  2. customthe completion of the reaction
  3. customthe reaction mixture was partitioned between ethyl acetate and 10% aqueous sodium chloride solution
  4. washThe organic layer was washed successively 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-84c8e25151fe40ce8016e223aa24f632
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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