Trifluoroacetic acid → 2-(4-(Dibutylcarbamoyl)-2-(4-(methoxycarbonyl)-2-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)phenyl)-1H-imidazol-1-yl)acetic acid

HRID 529000Notes

Reaction equation

HRID 529000 reaction equation
C([O:5][C:6](=[O:46])[CH2:7][N:8]1[CH:12]=[C:11]([C:13](=[O:23])[N:14]([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][CH2:16][CH2:17][CH3:18])[N:10]=[C:9]1[C:24]1[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][C:25]=1[C:34]([N:36]1[CH2:45][CH2:44][C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH2:37]1)=[O:35])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:19]([N:14]([CH2:15][CH2:16][CH2:17][CH3:18])[C:13]([C:11]1[N:10]=[C:9]([C:24]2[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][C:25]=2[C:34]([N:36]2[CH2:45][CH2:44][C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[CH2:37]2)=[O:35])[N:8]([CH2:7][C:6]([OH:46])=[O:5])[CH:12]=1)=[O:23])[CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71062593Methyl 4-(1-(2-tert-butoxy-2-oxoethyl)-4-(dibutylcarbamoyl)-1H-imidazol-2-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate

Product 1

HCID 710623632-(4-(Dibutylcarbamoyl)-2-(4-(methoxycarbonyl)-2-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)phenyl)-1H-imidazol-1-yl)acetic acidYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-(1-(2-tert-butoxy-2-oxoethyl)-4-(dibutylcarbamoyl)-1H-imidazol-2-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate (300 mg, 0.44 mmol) in DCM (3.0 mL) was added trifluoroacetic acid (3.0 mL) at 0° C. The reaction mixture was allowed to room temperature and stirring was continued for 1 h. The reaction mixture was concentrated in vacuo and the resulting residue was dissolved in DCM and washed with sat. NaHCO3 solution. The organic layer was dried over Na2SO4 and concentrated to give the title compound (200 mg, 80%). MS(ESI) m/z 575.4 (M+H)+.

Workup

  1. customwas allowed to room temperature
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionthe resulting residue was dissolved in DCM
  4. washwashed with sat. NaHCO3 solution
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9536c3b97727476d93339072b62029d8
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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