Acetic Acid → HCID 58508443, compound

HRID 454719Notes

Reaction equation

HRID 454719 reaction equation
C(O)(=O)C.C([O:12][C:13]1[CH:40]=[CH:39][C:38]([C:41]2[CH:46]=[CH:45][N:44]=[CH:43][CH:42]=2)=[CH:37][C:14]=1[C:15]([NH:17][C:18]1[CH:30]=[C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:28]=[CH:27][C:19]=1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:16])C1C=CC=CC=1.CO>[C].[Pd].C(Cl)(Cl)Cl>[OH:12][C:13]1[CH:40]=[CH:39][C:38]([CH:41]2[CH2:42][CH2:43][NH:44][CH2:45][CH2:46]2)=[CH:37][C:14]=1[C:15]([NH:17][C:18]1[CH:30]=[C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:28]=[CH:27][C:19]=1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:16]

Participants

6

Reactant 3

HCID 176Acetic Acid2×HCID 887MethanolHCID 66990236HCID 66990236, compound

Product 1

HCID 58508443HCID 58508443, compoundYield 55.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
75 °C

Procedure

To an acetic acid (20 mL) solution of tert-butyl 2-(2-(benzyloxy)-5-(pyridin-4-yl)benzamido)-4-phenylbenzoate (0.77 g), 10% palladium-carbon (0.35 g) was added, followed by stirring under hydrogen pressure (5 kg/cm2) at 70 to 80° C. for 7 hours. The reaction mixture was cooled to room temperature, and acetic acid, methanol, and chloroform were added thereto. The insoluble substance was removed by filtration. The solvent was removed under reduced pressure, and then chloroform and a saturated aqueous solution of sodium bicarbonate were added to the residue. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium 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 0.36 g of tert-butyl 2-(2-hydroxy-5-(piperidin-4-yl)benzamido)-4-phenylbenzoate as a white solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe insoluble substance was removed by filtration
  3. customThe solvent was removed under reduced pressure
  4. additionchloroform and a saturated aqueous solution of sodium bicarbonate were added to the residue
  5. customThe organic layer was separated
  6. washwashed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. additionDiisopropyl ether was added to the obtained residue
  10. filtrationthe solid substance was collected by filtration

Sources & evidence

ORD record
ord-587d1e16153e4b13940516c308d81542
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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