Trifluoroacetic acid → HCID 67513954, compound

HRID 473907Notes

Reaction equation

HRID 473907 reaction equation
[CH3:1][CH:2]([CH3:36])[CH2:3][O:4][C:5]([N:7]1[CH:11]=[CH:10][N:9]=[C:8]1[C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]=[CH:20][C:21]3[O:27][CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][C:22]=3[CH:35]=2)=[CH:14][CH:13]=1)=[O:6].FC(F)(F)C(O)=O>ClCCl>[O:27]1[C:21]2[CH:20]=[CH:19][C:18]([C:15]3[CH:14]=[CH:13][C:12]([C:8]4[N:7]([C:5]([O:4][CH2:3][CH:2]([CH3:36])[CH3:1])=[O:6])[CH:11]=[CH:10][N:9]=4)=[CH:17][CH:16]=3)=[CH:35][C:22]=2[CH2:23][NH:24][CH2:25][CH2:26]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 675140761,1-dimethylethyl 7-[4-(1-{[(2-methylpropyl)oxy]carbonyl}-1H-imidazol-2-yl)phenyl]-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

Product 1

HCID 67513954HCID 67513954, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl 7-[4-(1-{[(2-methylpropyl)oxy]carbonyl}-1H-imidazol-2-yl)phenyl]-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (0.30 g, 0.61 mmol) in dichloromethane (100 mL) was added trifluoroacetic acid (20 mL) and the reaction mixture was heated to reflux. After cooling to room temperature the solvent was evaporated. The residue was dissolved in ethyl acetate (250 mL). The organic layer was washed with saturated aqueous sodium bicarbonate (2×100 mL), brine, dried over anhydrous sodium sulfate then filtered and concentrated to give 2-methylpropyl 2-[4-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)phenyl]-1H-imidazole-1-carboxylate (0.22 g, 92%). MS (EI) for C23H25N3O3: 392 (MH+).

Workup

  1. temperaturethe reaction mixture was heated to reflux
  2. customwas evaporated
  3. dissolutionThe residue was dissolved in ethyl acetate (250 mL)
  4. washThe organic layer was washed with saturated aqueous sodium bicarbonate (2×100 mL), brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationthen filtered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-14cb4d6f84ce48adb151ef44b70ebeea
Source dataset
uspto-grants-2014_01
Patent number
US08637499B2

Reaction notes

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