Trifluoroacetic acid → 4-{[(4-Benzofuran-2-yl-phenylcarbamoyl)-(4-tert-butyl-phenyl)-methyl]-methyl-amino}-benzoic Acid

HRID 2371268Notes

Reaction equation

HRID 2371268 reaction equation
C([O:5][C:6](=[O:44])[C:7]1[CH:12]=[CH:11][C:10]([N:13]([CH:15]([C:26](=[O:43])[N:27]([C:34]2[O:42][C:38]3=[CH:39][CH:40]=[CH:41][C:37]3=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:16]2[CH:21]=[CH:20][C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:18][CH:17]=2)[CH3:14])=[CH:9][CH:8]=1)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[O:42]1[C:38]2=[CH:39][CH:40]=[CH:41][C:37]2=[CH:36][CH:35]=[C:34]1[N:27]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:26]([CH:15]([N:13]([CH3:14])[C:10]1[CH:9]=[CH:8][C:7]([C:6]([OH:44])=[O:5])=[CH:12][CH:11]=1)[C:16]1[CH:17]=[CH:18][C:19]([C:22]([CH3:25])([CH3:23])[CH3:24])=[CH:20][CH:21]=1)=[O:43]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 674866384-{[(4-Benzofuran-2-yl-phenylcarbamoyl)-(4-tert-butyl-phenyl)-methyl]methyl-amino}-benzoic Acid Tert-butyl Ester

Product 1

HCID 674860264-{[(4-Benzofuran-2-yl-phenylcarbamoyl)-(4-tert-butyl-phenyl)-methyl]-methyl-amino}-benzoic AcidYield 108.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-{[(4-Benzofuran-2-yl-phenylcarbamoyl)-(4-tert-butyl-phenyl)-methyl]-methyl-amino}-benzoic acid tert-butyl ester (˜140 mg, 0.19 mmol) was taken up in 5 mL of dichloromethane followed by addition of 0.5 mL of TFA and stirred for 16 h at RT. Removal of the organic layer and water was added to give a precipitate, which was filtered to give 110 mg (100%) of pinkish solids. LCMS (M−1=531.1).

Workup

  1. customRemoval of the organic layer and water
  2. additionwas added
  3. customto give a precipitate, which
  4. filtrationwas filtered

Sources & evidence

ORD record
ord-f4368d62d6a347cc92d61658b2bd96e9
Source dataset
uspto-grants-2014_04
Patent number
US08710236B2

Reaction notes

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