Trifluoroacetic acid → 4-{[(4-tert-Butyl-phenyl)-(4-iodo-phenylcarbamoyl)-methyl]-amino}-benzoic Acid

HRID 2371264Notes

Reaction equation

HRID 2371264 reaction equation
C([O:5][C:6](=[O:35])[C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH:14]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:27][CH:26]=2)[C:15](=[O:24])[NH:16][C:17]2[CH:22]=[CH:21][C:20]([I:23])=[CH:19][CH:18]=2)=[CH:9][CH:8]=1)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[C:31]([C:28]1[CH:27]=[CH:26][C:25]([CH:14]([NH:13][C:10]2[CH:9]=[CH:8][C:7]([C:6]([OH:35])=[O:5])=[CH:12][CH:11]=2)[C:15](=[O:24])[NH:16][C:17]2[CH:22]=[CH:21][C:20]([I:23])=[CH:19][CH:18]=2)=[CH:30][CH:29]=1)([CH3:34])([CH3:32])[CH3:33]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 674865594-{[(4-tert-Butyl-phenyl)-(4-iodo-phenylcarbamoyl)-methyl]-amino}-benzoic Acid Tert-butyl Ester

Product 1

HCID 674867274-{[(4-tert-Butyl-phenyl)-(4-iodo-phenylcarbamoyl)-methyl]-amino}-benzoic AcidYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-{[(4-tert-Butyl-phenyl)-(4-iodo-phenylcarbamoyl)-methyl]-amino}-benzoic acid tert-butyl ester (430 mg, 0.74 mmol) was taken up in 10 mL of dichloromethane followed by addition of 1 mL of TFA and stirred for 16 h at RT. Removal of the organic layer under reduced pressure followed by addition of water to the precipitate. The solids were filtered to give 340 mg (87%) of white solids. 1H NMR showed the compound to be very clean and sufficient for the following step. LCMS (M+1=529.6).

Workup

  1. customRemoval of the organic layer under reduced pressure
  2. additionfollowed by addition of water to the precipitate
  3. filtrationThe solids were filtered

Sources & evidence

ORD record
ord-ad3408bf578d472590fc223f78b6fbeb
Source dataset
uspto-grants-2014_04
Patent number
US08710236B2

Reaction notes

Loading…