Trifluoroacetic acid → 2-(5-(((2-(Dimethylamino)ethyl)(methyl)amino)methyl)-2-hydroxybenzamido)-4-phenylbenzoic acid

HRID 454648Notes

Reaction equation

HRID 454648 reaction equation
FC(F)(F)C(O)=O.[CH3:8][N:9]([CH3:47])[CH2:10][CH2:11][N:12]([CH2:14][C:15]1[CH:16]=[CH:17][C:18]([O:43]COC)=[C:19]([CH:42]=1)[C:20]([NH:22][C:23]1[CH:35]=[C:34]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:33]=[CH:32][C:24]=1[C:25]([O:27]C(C)(C)C)=[O:26])=[O:21])[CH3:13]>>[CH3:8][N:9]([CH3:47])[CH2:10][CH2:11][N:12]([CH2:14][C:15]1[CH:16]=[CH:17][C:18]([OH:43])=[C:19]([CH:42]=1)[C:20]([NH:22][C:23]1[CH:35]=[C:34]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:33]=[CH:32][C:24]=1[C:25]([OH:27])=[O:26])=[O:21])[CH3:13]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66991111Tert-butyl 2-(5-(((2-(dimethylamino)ethyl)(methyl)amino)methyl)-2-(methoxymethoxy)benzamido)-4-phenylbenzoate

Product 1

HCID 585085472-(5-(((2-(Dimethylamino)ethyl)(methyl)amino)methyl)-2-hydroxybenzamido)-4-phenylbenzoic acidYield 78.7%

Procedure

Trifluoroacetic acid (5.0 mL) was added to the obtained tert-butyl 2-(5-(((2-(dimethylamino)ethyl)(methyl)amino)methyl)-2-(methoxymethoxy)benzamido)-4-phenylbenzoate (0.070 g), followed by stirring at room temperature for 8 hours. The solvent was evaporated under reduced pressure, and water and ethyl acetate were added to the residue. After adjusting the pH to 6.3 with a saturated aqueous solution of sodium bicarbonate, the organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. Diisopropyl ether was added to the obtained residue, and the solid substance was collected by filtration to obtain 0.045 g of 2-(5-(((2-(dimethylamino)ethyl)(methyl)amino)methyl)-2-hydroxybenzamido)-4-phenylbenzoic acid as a white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure, and water and ethyl acetate
  2. additionwere added to the residue
  3. customthe organic layer was separated
  4. washwashed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. additionDiisopropyl ether was added to the obtained residue
  8. filtrationthe solid substance was collected by filtration

Sources & evidence

ORD record
ord-66147b111c8d4441af41d68c2b85d242
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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