Trifluoroacetic acid → HCID 86729761, compound

HRID 2272604Notes

Reaction equation

HRID 2272604 reaction equation
[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([CH2:16][NH:17][C:18](=[O:29])[CH:19]([NH:21]C(=O)OC(C)(C)C)[CH3:20])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2].C(O)(C(F)(F)F)=O>>[NH2:21][CH:19]([CH3:20])[C:18]([NH:17][CH2:16][C:12]1[CH:13]=[CH:14][C:15]2[N:3]([CH2:1][CH3:2])[C:4]3[C:9]([C:10]=2[CH:11]=1)=[CH:8][CH:7]=[CH:6][CH:5]=3)=[O:29]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86729760HCID 86729760, compound

Product 1

HCID 86729761HCID 86729761, compoundYield 100%

Procedure

A solution of the compound obtained in Step 1 (324 mg, 0.82 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 2-amino-N-((9-ethyl-9H-carbazol-3-yl)methyl)propanamide (242 mg, 0.819 mmol, 100%) 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-7607df26895a4dccb3de9c06c1199f23
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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