Ammonium Acetate → HCID 178522787, compound

HRID 1797000Notes

Reaction equation

HRID 1797000 reaction equation
C([O-])(=O)C.[NH4+:5].[CH2:6]([O:13][C:14](=[O:39])[NH:15][CH2:16][CH:17]1[CH2:22][CH2:21][CH:20]([C:23](=O)[NH:24][CH2:25][C:26](=O)[C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=2)[CH2:19][CH2:18]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(O)(=O)C>[CH2:6]([O:13][C:14](=[O:39])[NH:15][CH2:16][CH:17]1[CH2:22][CH2:21][CH:20]([C:23]2[NH:24][CH:25]=[C:26]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=3)[N:5]=2)[CH2:19][CH2:18]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 12154029{4-[2-Oxo-2-(3-trifluoromethyl-phenyl)-ethylcarbamoyl]-cyclohexylmethyl}-carbamic acid benzyl ester

Product 1

HCID 178522787HCID 178522787, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ammonium acetate (26 g, 0.34 mol) was added to a solution of {4-[2-Oxo-2-(3-trifluoromethyl-phenyl)-ethylcarbamoyl]-cyclohexylmethyl}-carbamic acid benzyl ester (5.4 g, 0.0113 mol) in acetic acid. The resulting homogeneous mixture was refluxed overnight and then concentrated under reduced pressure. The residue was partitioned between 10% NaOH and EtOAc (1:1) and the EtOAc layer was washed with 10% NaOH (3×) and brine. The EtOAc was dried (Na2SO4) and concentrated under reduced pressure to give {4-[4-(3-Trifluoromethyl-phenyl)-1H-imidazol-2-yl]-cyclohexylmethyl}-carbamic acid benzyl ester. 1H NMR (CDCl3): δ 1.02–1.18 (m, 2H), 1.46–1.62 (m, 3H), 1.86–1.96 (m, 2H), 2.12–2.21 (m, 2H), 2.74 (m, 1H), 3.10 (t, J=6 Hz, 2H), 4.91 (t, 1H, N—H), 5.10 (s, 2H), 7.22 (s, 1H), 7.32–7.37 (m, 5H), 7.45 (d, J=4.9 hz, 2H), 7.87 (m, 1H), 7.95 (s, 1H). MS 458 (M+H)+

Workup

  1. temperatureThe resulting homogeneous mixture was refluxed overnight
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was partitioned between 10% NaOH and EtOAc (1:1)
  4. washthe EtOAc layer was washed with 10% NaOH (3×) and brine
  5. dry with materialThe EtOAc was dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-06f1edf21cf34470914cf9f97946374d
Source dataset
uspto-grants-2006_04
Patent number
US07034034B2

Reaction notes

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