Trifluoroacetic acid → HCID 58508900, compound

HRID 454570Notes

Reaction equation

HRID 454570 reaction equation
FC(F)(F)C(O)=O.C([O:11][C:12]1[CH:46]=[CH:45][C:44]([C:47]2[CH:48]=[N:49][CH:50]=[CH:51][CH:52]=2)=[CH:43][C:13]=1[C:14]([NH:16][C:17]1[CH:26]=[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[N:33](C(OC(C)(C)C)=O)[CH2:34][CH3:35])[CH:24]=[CH:23][C:18]=1[C:19]([O:21]C)=[O:20])=[O:15])(=O)C>>[CH2:34]([NH:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[C:25]1[CH:24]=[CH:23][C:18]([C:19]([OH:21])=[O:20])=[C:17]([NH:16][C:14](=[O:15])[C:13]2[CH:43]=[C:44]([C:47]3[CH:48]=[N:49][CH:50]=[CH:51][CH:52]=3)[CH:45]=[CH:46][C:12]=2[OH:11])[CH:26]=1)[CH3:35]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66990700HCID 66990700, compound

Product 1

HCID 58508900HCID 58508900, compound

Conditions

Temperature
52.5 °C

Procedure

A trifluoroacetic acid (4.0 mL) solution of the obtained methyl 2-(2-acetoxy-5-(pyridin-3-yl)benzamido)-4-(2-((tert-butoxycarbonyl)(ethyl)amino)phenyl)benzoate was stirred at room temperature for 2 hours and 30 minutes. The solvent was evaporated under reduced pressure, and toluene was added thereto. The solvent was evaporated under reduced pressure, and diisopropyl ether was added to the obtained residue. The solid substance was collected by filtration. Dioxane (4.0 mL) and a 1 mol/L aqueous solution of sodium hydroxide (0.40 mL) were added to the obtained solid substance, followed by stirring at 50 to 55° C. for 2 hours. The reaction mixture was cooled to room temperature and then adjusted to a pH of 7.4 with 1 mol/L hydrochloric acid. The solvent was evaporated under reduced pressure, and water was added to the obtained residue. The solid substance was collected by filtration to obtain 0.032 g of 4-(2-(ethylamino)phenyl)-2-(2-hydroxy-5-(pyridin-3-yl)benzamido)benzoic acid as a white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure, and toluene
  2. additionwas added
  3. customThe solvent was evaporated under reduced pressure, and diisopropyl ether
  4. additionwas added to the obtained residue
  5. filtrationThe solid substance was collected by filtration
  6. additionDioxane (4.0 mL) and a 1 mol/L aqueous solution of sodium hydroxide (0.40 mL) were added to the obtained solid substance
  7. temperatureThe reaction mixture was cooled to room temperature
  8. customThe solvent was evaporated under reduced pressure, and water
  9. additionwas added to the obtained residue
  10. filtrationThe solid substance was collected by filtration

Sources & evidence

ORD record
ord-d1efa375352c4ae7ae1b6b72589f813c
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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