Ethyl Acetate → HCID 22242926, compound

HRID 891778Notes

Reaction equation

HRID 891778 reaction equation
[C:1]([NH:9][CH2:10][C:11]1[N:12]=[C:13]([N:16]2[CH2:19][CH:18](OS(C)(=O)=O)[CH2:17]2)[S:14][CH:15]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25]([O-:28])(=[S:27])[CH3:26].[K+].C(OCC)(=O)C>CN(C)C=O>[C:25]([S:27][CH:18]1[CH2:17][N:16]([C:13]2[S:14][CH:15]=[C:11]([CH2:10][NH:9][C:1](=[O:8])[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[N:12]=2)[CH2:19]1)(=[O:28])[CH3:26]

Participants

5

Reactant 3

HCID 8857Ethyl Acetate2×HCID 22242986HCID 22242986, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 22242926HCID 22242926, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-[4-(benzoylaminomethyl)-1,3-thiazol-2-yl]-3-methanesulfonyloxyazetidine (739 mg, 2.01 mmol) (obtained as described in Reference Example 64(3)) in dimethylformamide (20 ml) was added potassium thioacetate (1.38 g, 12.1 mmol) at room temperature, and the mixture was stirred in an oil bath (90° C.) for 3.5 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)→ethyl acetate as the eluant to afford 3-acetylthio-1-[4-(benzoylaminomethyl)-1,3-thiazol-2-yl]azetidine (698 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-6406334a35834a828793cbc9ffe17630
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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