Trifluoroacetic acid → HCID 70097566, compound

HRID 2368292Notes

Reaction equation

HRID 2368292 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[N:6]=[C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[S:8][C:9]=1[NH:10]C(OC(C)(C)C)=O)=[O:4].FC(F)(F)C(O)=O>ClCCl>[CH3:1][NH:2][C:3]([C:5]1[N:6]=[C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[S:8][C:9]=1[NH2:10])=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70098496HCID 70098496, compound

Product 1

HCID 70097566HCID 70097566, compoundYield 42.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-tert-butoxycarbonylamino-2-pyridin-2-yl-thiazole-4-carboxylic acid methylamide (34 mg, 0.10 mmol) in dichloromethane (0.5 ml) was treated with trifluoroacetic acid (0.5 ml) and stirred at ambient temperature for 3 h. After solvent evaporation, the residue was dissolved in ethyl acetate and washed with NaOH (1N aqueous solution), water and brine. The organic layer was dried and the solvent was evaporated. The remaining residue was suspended in diethylether, sucked off, and the remaining material was dried to yield the product as yellow solid (10 mg, 42%).

Workup

  1. customAfter solvent evaporation
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with NaOH (1N aqueous solution), water and brine
  4. customThe organic layer was dried
  5. customthe solvent was evaporated
  6. customthe remaining material was dried

Sources & evidence

ORD record
ord-35bd0c88376b43208627fed2f0c608de
Source dataset
uspto-grants-2014_04
Patent number
US08703768B2

Reaction notes

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