Trifluoroacetic acid → HCID 58508914, compound

HRID 454551Notes

Reaction equation

HRID 454551 reaction equation
C1(SC)C=CC=CC=1.FC(F)(F)C(O)=O.C([O:23][C:24]1[CH:51]=[C:50]([C:52]2[CH:56]=[CH:55][O:54][CH:53]=2)[CH:49]=[CH:48][C:25]=1[C:26]([NH:28][C:29]1[CH:41]=[C:40]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:39]=[CH:38][C:30]=1[C:31]([O:33]C(C)(C)C)=[O:32])=[O:27])C1C=CC=CC=1>>[O:54]1[CH:55]=[CH:56][C:52]([C:50]2[CH:49]=[CH:48][C:25]([C:26]([NH:28][C:29]3[CH:41]=[C:40]([C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)[CH:39]=[CH:38][C:30]=3[C:31]([OH:33])=[O:32])=[O:27])=[C:24]([OH:23])[CH:51]=2)=[CH:53]1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7520ThioanisoleHCID 66991530HCID 66991530, compound

Product 1

HCID 58508914HCID 58508914, compoundYield 28.8%

Procedure

Thioanisole (0.82 mL) and trifluoroacetic acid (2.6 mL) were added to the obtained tert-butyl 2-(2-(benzyloxy)-4-(furan-3-yl)benzamido)-4-phenylbenzoate (0.076 g), followed by stirring at room temperature for 3 hours and 20 minutes. The solvent was evaporated under reduced pressure, and a 2 mol/L aqueous solution of sodium hydroxide and toluene were added to the residue. The aqueous layer was separated and adjusted to a pH of 4.5 with 6 mol/L hydrochloric acid. The solid substance was collected by filtration to obtain 0.016 g of 2-(4-(furan-3-yl)-2-hydroxybenzamido)-4-phenylbenzoic acid as a brown solid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additiona 2 mol/L aqueous solution of sodium hydroxide and toluene were added to the residue
  3. customThe aqueous layer was separated
  4. filtrationThe solid substance was collected by filtration

Sources & evidence

ORD record
ord-1863c4c0b3e84cd7827f7cc97b694043
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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