Trifluoroacetic acid → HCID 68193221, compound

HRID 1626803Notes

Reaction equation

HRID 1626803 reaction equation
C([O:8][C:9]1[C:10]([C:40]([O:42]C(C)(C)C)=[O:41])=[N:11][C:12]([CH2:16][CH:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[CH:33][C:32]([C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:31][N:30]=4)=[CH:25][CH:24]=3)[CH2:19][CH2:18]2)=[N:13][C:14]=1[CH3:15])C1C=CC=CC=1.FC(F)(F)C(O)=O>ClCCl>[CH2:38]([O:37][C:35]([C:32]1[CH:33]=[CH:34][C:29]([C:26]2[CH:25]=[CH:24][C:23]([N:20]3[CH2:21][CH2:22][CH:17]([CH2:16][C:12]4[N:11]=[C:10]([C:40]([OH:42])=[O:41])[C:9]([OH:8])=[C:14]([CH3:15])[N:13]=4)[CH2:18][CH2:19]3)=[CH:28][CH:27]=2)=[N:30][CH:31]=1)=[O:36])[CH3:39]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68196371HCID 68196371, compound

Product 1

HCID 68193221HCID 68193221, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 5-(benzyloxy)-2-[(1-{4-[5-(ethoxycarbonyl)pyridin-2-yl]phenyl}piperidin-4-yl)methyl]-6-methylpyrimidine-4-carboxylate (0.25 g, 0.40 mmol) was dissolved in dichloromethane (5 mL), and trifluoroacetic acid (10 mL) was added, followed by stirring at room temperature for 12 hours. The reaction solution was concentrated under reduced pressure, and a saturated aqueous sodium hydrogencarbonate solution was added, followed by extraction with ethyl acetate. After the organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure to afford 2-[(1-{4-[5-(ethoxycarbonyl)pyridin-2-yl]phenyl}piperidin-4-yl)methyl]-5-hydroxy-6-methylpyrimidine-4-carboxylic acid.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additiona saturated aqueous sodium hydrogencarbonate solution was added
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-5fdd51766a8740f4ba3fde827451d835
Source dataset
uspto-grants-2014_07
Patent number
US08785462B2

Reaction notes

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