Trifluoroacetic acid → HCID 62671211, compound

HRID 2272598Notes

Reaction equation

HRID 2272598 reaction equation
[C:1]([C:3]1[CH:23]=[CH:22][C:6]([CH2:7][NH:8][C:9](=[O:21])[CH:10]([CH3:20])[CH2:11][NH:12]C(=O)OC(C)(C)C)=[CH:5][CH:4]=1)#[N:2].C(O)(C(F)(F)F)=O>>[NH2:12][CH2:11][CH:10]([CH3:20])[C:9]([NH:8][CH2:7][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:23][CH:22]=1)=[O:21]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86729756HCID 86729756, compound

Product 1

HCID 62671211HCID 62671211, compoundYield 74%

Procedure

A solution of the compound obtained in Step 1 (221 mg, 0.70 mmol) in TFA (1 mL, 12.98 mmol) was stirred at room temperature for 15 min, and 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 3-amino-N-(4-cyanobenzyl)-2-methylpropanamide (112 mg, 0.515 mmol, 74.0%) as a white powder.

Workup

  1. concentrationconcentrated 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-184b69aa8cc84480816e064707f2ceaf
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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