Trifluoroacetic acid → HCID 59059305, compound

HRID 2415752Notes

Reaction equation

HRID 2415752 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:16]2[O:20][N:19]=[C:18]([C:21]3[CH:22]=[CH:23][C:24]([N:27]4[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]4)=[N:25][CH:26]=3)[N:17]=2)[CH2:11][C:12]([NH:14][OH:15])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:16]2[O:20][N:19]=[C:18]([C:21]3[CH:26]=[N:25][C:24]([N:27]4[CH2:28][CH2:29][NH:30][CH2:31][CH2:32]4)=[CH:23][CH:22]=3)[N:17]=2)[CH2:11][C:12]([NH:14][OH:15])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59059309HCID 59059309, compound

Product 1

HCID 59059305HCID 59059305, compoundYield 9.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the title compound from Example 32 (0.37 g, 0.7 mmol) in dichloromethane (5 mL) was added trifluoroacetic acid (5 mL) and the reaction was stirred at room temperature for 1.5 hours. The solvent was removed in vacuo and the residue was azeotroped with toluene. The residue was then dissolved in ethyl acetate (30 mL) and washed with saturated aqueous sodium bicarbonate solution (30 mL) followed by 10% aqueous citric acid solution (30 mL). The acidic aqueous layer was basified to pH 7 with saturated aqueous sodium bicarbonate solution and then extracted with ethyl acetate (3×30 mL). The combined organic extracts were washed with water (30 mL), dried (MgSO4) and the solvent was removed in vacuo to give the title compound as a viscous oil (0.03 g).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was azeotroped with toluene
  3. dissolutionThe residue was then dissolved in ethyl acetate (30 mL)
  4. washwashed with saturated aqueous sodium bicarbonate solution (30 mL)
  5. extractionextracted with ethyl acetate (3×30 mL)
  6. washThe combined organic extracts were washed with water (30 mL)
  7. dry with materialdried (MgSO4)
  8. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-0148229f38b343f291ebd99ba90a6742
Source dataset
uspto-grants-2004_11
Patent number
US06821972B2

Reaction notes

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