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

HRID 73238Notes

Reaction equation

HRID 73238 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-3f315f5b23ce45d08c2f865e769c43be
Source dataset
uspto-grants-2014_09
Patent number
US08829034B2

Reaction notes

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