Trifluoroacetic acid → N-(3-amino-2-methylpropyl)-4-cyanobenzenesulfonamide

HRID 2272582Notes

Reaction equation

HRID 2272582 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][CH2:13][CH:14]([CH3:24])[CH2:15][NH:16]C(=O)OC(C)(C)C)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2].C(O)(C(F)(F)F)=O>>[NH2:16][CH2:15][CH:14]([CH3:24])[CH2:13][NH:12][S:9]([C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=1)(=[O:11])=[O:10]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86729742HCID 86729742, compound

Product 1

HCID 86729743N-(3-amino-2-methylpropyl)-4-cyanobenzenesulfonamideYield 65.6%

Procedure

A solution of the compound obtained in Step 1 (273 mg, 0.77 mmol) in TFA (1 mL, 12.98 mmol) was stirred at room temperature for min, and the mixture was concentrated under reduced pressure. To the residue were added ethyl acetate and 1N aqueous sodium hydroxide solution, and the organic layer was separated. The organic layer was washed with water and saturated brine, and dried, and the solvent was evaporated under reduced pressure to give N-(3-amino-2-methylpropyl)-4-cyanobenzenesulfonamide (128 mg, 0.505 mmol, 65.4%) as a white powder.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additionTo the residue were added ethyl acetate and 1N aqueous sodium hydroxide solution
  3. customthe organic layer was separated
  4. washThe organic layer was washed with water and saturated brine
  5. customdried
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-afeae13304ce47a6bbd456ef5cc0c1ba
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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