Hydrochloric Acid → N-(5-tert-butyl-isoxazol-3-yl)-2-methyl-2-(piperidin-3-ylmethylsulfanyl)-propionamide

HRID 73242Notes

Reaction equation

HRID 73242 reaction equation
C(OC(N1CCC[CH:10]([C:14]([S:28][CH2:29][CH3:30])([C:16](=[O:27])[NH:17][C:18]2[CH:22]=[C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])[O:20][N:19]=2)[CH3:15])C1)=O)(C)(C)C.Cl>C(Cl)Cl.C([O-])(O)=O.[Na+]>[C:23]([C:21]1[O:20][N:19]=[C:18]([NH:17][C:16](=[O:27])[C:14]([CH3:10])([S:28][CH2:29][CH:30]2[CH2:10][CH2:14][CH2:16][NH:17][CH2:18]2)[CH3:15])[CH:22]=1)([CH3:24])([CH3:25])[CH3:26]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67097461HCID 67097461, compound

Product 1

HCID 59704015N-(5-tert-butyl-isoxazol-3-yl)-2-methyl-2-(piperidin-3-ylmethylsulfanyl)-propionamideYield 158.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 288 mg (0.65 mmol) of 3-[1-(5-tert-butyl-isoxazol-3-ylcarbamoyl)-1-methyl-ethylsulfanylmethyl]-piperidine-1-carboxylic acid tert-butyl ester (synthesized according to Method H, step 1) in DCM (5 mL) were added 1.1 mL of HCl (2M solution in dioxane). The reaction was stirred at room temperature for 16 h. The mixture was diluted with saturated aqueous NaHCO3 solution (5 mL), the organic layer was separated and dried over Na2SO4. Filtration and concentration of the filtrate under reduced pressure afforded 175 mg of N-(5-tert-butyl-isoxazol-3-yl)-2-methyl-2-(piperidin-3-ylmethylsulfanyl)-propionamide.

Workup

  1. customthe organic layer was separated
  2. dry with materialdried over Na2SO4
  3. filtrationFiltration and concentration of the filtrate under reduced pressure

Sources & evidence

ORD record
ord-8b6e6cb3a36544eeb8251436226dc56d
Source dataset
uspto-grants-2014_09
Patent number
US08829034B2

Reaction notes

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