Trifluoroacetic acid → Methyl 2-(2-(benzyloxy)-5-(piperidin-4-yl)benzamido)-4-phenylbenzoate

HRID 454573Notes

Reaction equation

HRID 454573 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:15][C:16]1[CH:40]=[CH:39][C:38]([CH:41]2[CH2:46][CH2:45][N:44](C(OC(C)(C)C)=O)[CH2:43][CH2:42]2)=[CH:37][C:17]=1[C:18]([NH:20][C:21]1[CH:30]=[C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:28]=[CH:27][C:22]=1[C:23]([O:25][CH3:26])=[O:24])=[O:19])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(Cl)(Cl)Cl>[CH2:8]([O:15][C:16]1[CH:40]=[CH:39][C:38]([CH:41]2[CH2:42][CH2:43][NH:44][CH2:45][CH2:46]2)=[CH:37][C:17]=1[C:18]([NH:20][C:21]1[CH:30]=[C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:28]=[CH:27][C:22]=1[C:23]([O:25][CH3:26])=[O:24])=[O:19])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66990151Methyl 2-(2-(benzyloxy)-5-(1-(tert-butoxycarbonyl)piperidin-4-yl)benzamido)-4-phenylbenzoate

Product 1

HCID 66990546Methyl 2-(2-(benzyloxy)-5-(piperidin-4-yl)benzamido)-4-phenylbenzoateYield 94.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Trifluoroacetic acid (1.0 mL) was added to a chloroform (2.0 mL) solution of the obtained methyl 2-(2-(benzyloxy)-5-(1-(tert-butoxycarbonyl)piperidin-4-yl)benzamido)-4-phenylbenzoate (0.19 g), followed by stirring at room temperature for 1 hour and 30 minutes. The solvent was evaporated under reduced pressure, and water was added to the residue. After adjusting the pH to 7.4 with a saturated aqueous solution of sodium bicarbonate, chloroform was added thereto. 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 to obtain 0.15 g of methyl 2-(2-(benzyloxy)-5-(piperidin-4-yl)benzamido)-4-phenylbenzoate as a white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure, and water
  2. additionwas added to the residue
  3. additionwas added
  4. customThe organic layer was separated
  5. washwashed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d7aeab029bcb4db5824144290eeb0704
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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