Hydrochloric Acid → HCID 90204098, compound

HRID 1480180Notes

Reaction equation

HRID 1480180 reaction equation
[CH2:1]([O:8][CH2:9][C:10]([NH:18]S(C(C)(C)C)=O)([C:12]1[N:16]=[C:15]([CH3:17])[O:14][N:13]=1)[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.O1CCOCC1>CO>[CH2:1]([O:8][CH2:9][C:10]([C:12]1[N:16]=[C:15]([CH3:17])[O:14][N:13]=1)([NH2:18])[CH3:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 90203919HCID 90203919, compound

Product 1

HCID 90204098HCID 90204098, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(1-(benzyloxy)-2-(5-methyl-1,2,4-oxadiazol-3-yl)propan-2-yl)-2-methylpropane-2-sulfinamide (example 112c, 1.2 g, 2.73 mmol) in methanol (15 ml) was added a 4.0M solution of hydrochloric acid in Dioxane (2.05 ml, 8.19 mmol). The reaction mixture was stirred at room temperature for 2 hours. Volatiles were removed in vacuo and the residue was dissolved in ethyl acetate. The organic phase was extracted with a 1.0M aqueous solution of sodium bicarbonate and the organic phase was collected. 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 heptane\ethyl acetate gradient to yield the title compound (577 mg, 85%) as a light yellow oil. MS (ESI, m/z): 248.6 (M+H+).

Workup

  1. customVolatiles were removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. extractionThe organic phase was extracted with a 1.0M aqueous solution of sodium bicarbonate
  4. customthe organic phase was collected
  5. extractionThe aqueous phase was back-extracted with ethyl acetate
  6. dry with materialThe combined organic phases were dried over sodium sulfate
  7. customevaporated down to dryness
  8. customThe crude material was purified by flash chromatography on silica eluting with a heptane\ethyl acetate gradient

Sources & evidence

ORD record
ord-750db6b4bedf4389b9dfe10ff81c06e7
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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