Hydrochloric Acid → HCID 90204007, compound

HRID 1480303Notes

Reaction equation

HRID 1480303 reaction equation
CC(S([NH:7][CH:8]([C:14]1[O:15][C:16]([CH3:19])=[N:17][N:18]=1)[C:9]1([CH3:13])[CH2:12][O:11][CH2:10]1)=O)(C)C.Cl.O1CCOCC1>CO>[CH3:19][C:16]1[O:15][C:14]([CH:8]([C:9]2([CH3:13])[CH2:10][O:11][CH2:12]2)[NH2:7])=[N:18][N:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 90203672HCID 90203672, compound

Product 1

HCID 90204007HCID 90204007, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-methyl-N-[(5-methyl-1,3,4-oxadiazol-2-yl)-(3-methyloxetan-3-yl)methyl]propane-2-sulfinamide (example 245a, 1.23 g, 4.28 mmol) in methanol (20 ml) was added a 4M solution of hydrochloric acid in dioxane (1.61 ml, 6.42 mmol) and the reaction mixture was stirred at room temperature for 2 hours. Reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate. The organic phase was extracted with 5 ml of a 2M aqueous solution of sodium carbonate. The organic phase was collected and the aqueous phase was back-extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a dichloromethane/methanol gradient to yield the title compound (179 mg, 23%). MS (ESI, m/z): 184.5 (M+H+).

Workup

  1. customReaction mixture
  2. concentrationwas concentrated in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. extractionThe organic phase was extracted with 5 ml of a 2M aqueous solution of sodium carbonate
  5. customThe organic phase was collected
  6. extractionthe aqueous phase was back-extracted with ethyl acetate
  7. dry with materialThe combined organic phases were dried over sodium sulfate
  8. customevaporated down to dryness
  9. customThe crude material was purified by flash chromatography on silica eluting with a dichloromethane/methanol gradient

Sources & evidence

ORD record
ord-9197a3170aba4d288b87fee3cd827b10
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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