HCID 22242733, compound → HCID 22242720, compound

HRID 891710Notes

Reaction equation

HRID 891710 reaction equation
[C:1]([CH2:3][N:4]([CH:21]([CH3:23])[CH3:22])[C:5]([C:7]1[N:8]=[C:9]([N:12]2[CH2:15][CH:14](OS(C)(=O)=O)[CH2:13]2)[S:10][CH:11]=1)=[O:6])#[N:2].[C:24]([O-:27])(=[S:26])[CH3:25].[K+]>CN(C)C=O>[C:24]([S:26][CH:14]1[CH2:13][N:12]([C:9]2[S:10][CH:11]=[C:7]([C:5](=[O:6])[N:4]([CH2:3][C:1]#[N:2])[CH:21]([CH3:22])[CH3:23])[N:8]=2)[CH2:15]1)(=[O:27])[CH3:25]

Participants

4

Reactant 2

HCID 22242733HCID 22242733, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 22242720HCID 22242720, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-[4-(N-cyanomethyl-N-isopropyl-carbamoyl)-1,3-thiazol-2-yl]-3-methanesulfonyloxyazetidine (635 mg, 1.77 mmol) (obtained as described in Reference Example 49(5)) in dimethylformamide (19 ml) was added potassium thioacetate (1.21 g, 10.6 mmol) at room temperature, and the reaction mixture was stirred in an oil bath (90° C.) for 3 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 obtained 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-(N-cyanomethyl-N-isopropyl-carbamoyl)-1,3-thiazol-2-yl]azetidine (344 mg, yield 57%) 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 obtained residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-baee7b1662d84d23964aac0dfb65bd97
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

Loading…