Trifluoroacetic acid → HCID 67497465, compound

HRID 1628203Notes

Reaction equation

HRID 1628203 reaction equation
[O:1]=[C:2]([NH:19][C:20]1[O:24][N:23]=[C:22]([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)[CH:21]=1)[C@@H:3]([NH:11]C(=O)OC(C)(C)C)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:11][C@@H:3]([CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:2]([NH:19][C:20]1[O:24][N:23]=[C:22]([C:25]2[CH:26]=[CH:27][N:28]=[CH:29][CH:30]=2)[CH:21]=1)=[O:1]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70865441HCID 70865441, compound

Product 1

HCID 67497465HCID 67497465, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 25 ml flask was added (S)-tert-butyl 1-oxo-3-phenyl-1-(3-(pyridin-4-yl)isoxazol-5-ylamino)propan-2-ylcarbamate 3.3B (160 mg, 0.40 mmoles), 10 ml of CH2Cl2, and 5 ml of TFA. The reaction was stirred at room temperature for 3 hour at which time the solvent was removed with a stream of nitrogen. The crude material was then partitioned between 200 ml of DCM and 100 ml of saturated sodium bicarbonate. The organic solvent was removed by rotary evaporation to give (S)-2-amino-3-phenyl-N-(3-(pyridin-4-yl)isoxazol-5-yl)propanamide 3.3.C as a light yellow solid (100 mg, 81% yield).

Workup

  1. customwas removed with a stream of nitrogen
  2. customThe crude material was then partitioned between 200 ml of DCM and 100 ml of saturated sodium bicarbonate
  3. customThe organic solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-30a40efa770e45c0a8cdd070fc1727a9
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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