Trifluoroacetic acid → HCID 54286462, compound

HRID 600301Notes

Reaction equation

HRID 600301 reaction equation
[NH2:1][C@@H:2]([CH2:10][C:11]1[CH:12]=[N:13][C:14]([Br:17])=[CH:15][CH:16]=1)[C:3]([O:5]C(C)(C)C)=[O:4].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:1][C@@H:2]([CH2:10][C:11]1[CH:12]=[N:13][C:14]([Br:17])=[CH:15][CH:16]=1)[C:3]([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59665469HCID 59665469, compound

Product 1

HCID 54286462HCID 54286462, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-tert-Butyl 2-amino-3-(6-bromopyridin-3-yl)propanoate (4 g) was dissolved in DCM (20 mL) and the solution obtained was treated with TFA (20 mL). The mixture was stirred for 0.5 h, concentrated in vacuo, azeotroping with toluene, and loaded onto an NH2-silica cartridge. Non acidic impurities were eluted with acetonitrile, then the desired product was eluted with 10% acetic acid in acetonitrile. Solvent was removed in vacuo to give the sub-title compound (2.5 g).

Workup

  1. customthe solution obtained
  2. concentrationconcentrated in vacuo
  3. customazeotroping with toluene
  4. washNon acidic impurities were eluted with acetonitrile
  5. washthe desired product was eluted with 10% acetic acid in acetonitrile
  6. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-164f5d30fd2f47b99bc0065562212676
Source dataset
uspto-grants-2011_03
Patent number
US07902181B2

Reaction notes

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