Trifluoroacetic acid → 2-(2-Hydroxy-5-(methyl(2-(morpholin-4-yl)ethyl)amino)benzamido)-4-phenylbenzoic acid

HRID 454612Notes

Reaction equation

HRID 454612 reaction equation
FC(F)(F)C(O)=O.[OH:8][C:9]1[CH:36]=[CH:35][C:34]([N:37]([CH3:46])[CH2:38][CH2:39][N:40]2[CH2:45][CH2:44][O:43][CH2:42][CH2:41]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]>>[OH:8][C:9]1[CH:36]=[CH:35][C:34]([N:37]([CH3:46])[CH2:38][CH2:39][N:40]2[CH2:45][CH2:44][O:43][CH2:42][CH2:41]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

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58508749Tert-butyl 2-(2-hydroxy-5-(methyl(2-(morpholin-4-yl)ethyl)amino)benzamido)-4-phenylbenzoate

Product 1

HCID 585089032-(2-Hydroxy-5-(methyl(2-(morpholin-4-yl)ethyl)amino)benzamido)-4-phenylbenzoic acidYield 36.3%

Procedure

Trifluoroacetic acid (5.0 mL) was added to the obtained tert-butyl 2-(2-hydroxy-5-(methyl(2-(morpholin-4-yl)ethyl)amino)benzamido)-4-phenylbenzoate (0.074 g), followed by stirring at room temperature for 3 hours. The solvent was evaporated under reduced pressure, and water and chloroform were added to the residue. After adjusting the pH to 7.0 with a saturated aqueous solution of sodium bicarbonate, the organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined, and the resulting mixture was dried over anhydrous sodium sulfate. 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 0.024 g of 2-(2-hydroxy-5-(methyl(2-(morpholin-4-yl)ethyl)amino)benzamido)-4-phenylbenzoic acid as a yellow solid.

Workup

  1. customThe solvent was evaporated under reduced pressure, and water and chloroform
  2. additionwere added to the residue
  3. customthe organic layer was separated
  4. extractionthe aqueous layer was extracted with chloroform
  5. dry with materialthe resulting mixture was dried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure, and diisopropyl ether
  7. additionwas added to the obtained residue
  8. filtrationThe solid substance was collected by filtration

Sources & evidence

ORD record
ord-8b772fa0d329438b9b9dd1a47bf4da2a
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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