Trifluoroacetic acid → 2-(2-Hydroxy-5-(tetrahydrofuran-3-yl)benzamido)-4-phenylbenzoic acid

HRID 454587Notes

Reaction equation

HRID 454587 reaction equation
FC(F)(F)C(O)=O.[OH:8][C:9]1[CH:36]=[CH:35][C:34]([CH:37]2[CH2:41][CH2:40][O:39][CH2:38]2)=[CH:33][C:10]=1[C:11]([NH:13][C:14]1[CH:26]=[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:24]=[CH:23][C:15]=1[C:16]([O:18]C(C)(C)C)=[O:17])=[O:12]>C(Cl)Cl>[OH:8][C:9]1[CH:36]=[CH:35][C:34]([CH:37]2[CH2:41][CH2:40][O:39][CH2:38]2)=[CH:33][C:10]=1[C:11]([NH:13][C:14]1[CH:26]=[C:25]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:24]=[CH:23][C:15]=1[C:16]([OH:18])=[O:17])=[O:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58508894Tert-butyl 2-(2-hydroxy-5-(tetrahydrofuran-3-yl)benzamido)-4-phenylbenzoate

Product 1

HCID 585088282-(2-Hydroxy-5-(tetrahydrofuran-3-yl)benzamido)-4-phenylbenzoic acidYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2 mL) was added to a methylene chloride (5 mL) solution of the obtained tert-butyl 2-(2-hydroxy-5-(tetrahydrofuran-3-yl)benzamido)-4-phenylbenzoate (0.027 g), followed by stirring at room temperature for 3 hours. The solvent was evaporated under reduced pressure, and diisopropyl ether was added to the obtained residue. The solid substance was collected by filtration to obtain 0.023 g of 2-(2-hydroxy-5-(tetrahydrofuran-3-yl)benzamido)-4-phenylbenzoic acid as a white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure, and diisopropyl ether
  2. additionwas added to the obtained residue
  3. filtrationThe solid substance was collected by filtration

Sources & evidence

ORD record
ord-dcada9b33feb4dc4b5dcb44713952668
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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