Potassium ethanethioate → thioacetic acid S-[1-(5-tert-butyl-isoxazol-3-ylcarbamoyl)-1-methyl-ethyl]ester

HRID 2077102Notes

Reaction equation

HRID 2077102 reaction equation
Br[C:2]([CH3:16])([CH3:15])[C:3]([NH:5][C:6]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[O:8][N:7]=1)=[O:4].[C:17]([O-:20])(=[S:19])[CH3:18].[K+]>CN(C=O)C.C(OCC)C>[C:11]([C:9]1[O:8][N:7]=[C:6]([NH:5][C:3]([C:2]([S:19][C:17](=[O:20])[CH3:18])([CH3:16])[CH3:15])=[O:4])[CH:10]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 2

HCID 23670855Potassium ethanethioateHCID 596626262-bromo-N-(5-tert-butyl-isoxazol-3-yl)-2-methyl-propionamide

Product 1

HCID 59703935thioacetic acid S-[1-(5-tert-butyl-isoxazol-3-ylcarbamoyl)-1-methyl-ethyl]esterYield 77%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 200 mg (0.69 mmol) of 2-bromo-N-(5-tert-butyl-isoxazol-3-yl)-2-methyl-propionamide (prepared as described in Method B, step 2) in DMF (3 mL) were added 157 mg (1.4 mmol) of potassium thioacetate. The reaction was stirred at room temperature for 3 h. The reaction mixture was diluted with diethyl ether (5 mL) and washed with 2M aqueous HCl solution (5 mL). The organic layer was dried over Na2SO4. Filtration and concentration under reduced pressure afforded 151 mg of thioacetic acid S-[1-(5-tert-butyl-isoxazol-3-ylcarbamoyl)-1-methyl-ethyl]ester.

Workup

  1. washwashed with 2M aqueous HCl solution (5 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationFiltration and concentration under reduced pressure

Sources & evidence

ORD record
ord-77b7712e05654800959132fcb5dc558e
Source dataset
uspto-grants-2011_04
Patent number
US07928123B2

Reaction notes

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