Hydrochloric Acid → 3-Amino-3-cyclopropylbutanamide

HRID 1480325Notes

Reaction equation

HRID 1480325 reaction equation
[CH:1]1([C:4]([NH:10]S(C(C)(C)C)=O)([CH3:9])[CH2:5][C:6]([NH2:8])=[O:7])[CH2:3][CH2:2]1.Cl.O1CCOCC1>CO>[NH2:10][C:4]([CH:1]1[CH2:3][CH2:2]1)([CH3:9])[CH2:5][C:6]([NH2:8])=[O:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 902035133-(Tert-butylsulfinylamino)-3-cyclopropyl-butanamide

Product 1

HCID 836818103-Amino-3-cyclopropylbutanamideYield 83.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-cyclopropyl-3-(1,1-dimethylethylsulfinamido)butanamide (442 mg, 1.79 mmol) in methanol (8 ml) was added a 4.0M solution of hydrochloric acid in dioxane (1.35 ml, 5.38 mmol) and the reaction mixture was stirred at room temperature for 1 h. Volatiles were removed in vacuo and the residue was dissolved in ethyl acetate. The organic phase was extracted with 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 gradient of dichloromethane/(solution of 3% aq. NH3 in methanol) to yield the title compound (213 mg, 83%); MS (ESI, m/z): 143.1 (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 2M aqueous solution of sodium carbonate
  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 gradient of dichloromethane/(solution of 3% aq. NH3 in methanol)

Sources & evidence

ORD record
ord-4959bd07df1d48b6bf42ff67489adeff
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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