Trifluoroacetic acid → HCID 11720107, compound

HRID 2054173Notes

Reaction equation

HRID 2054173 reaction equation
C(O[N:6]([CH2:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]([CH:21]2[CH2:26][CH2:25][N:24]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([S:34][C:35]4[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=4)=[CH:30][CH:29]=3)[CH2:23][CH2:22]2)[CH:15]=1)=[O:12])[C:7](C)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl.C([O-])(O)=O.[Na+]>[CH3:42][O:41][C:38]1[CH:39]=[CH:40][C:35]([S:34][C:31]2[CH:30]=[CH:29][C:28]([CH2:27][N:24]3[CH2:25][CH2:26][CH:21]([C:16]4[CH:15]=[C:14]([NH:13][C:11](=[O:12])[CH2:10][NH:6][CH3:7])[CH:19]=[CH:18][C:17]=4[CH3:20])[CH2:22][CH2:23]3)=[CH:33][CH:32]=2)=[CH:36][CH:37]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86604273HCID 86604273, compound

Product 1

HCID 11720107HCID 11720107, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

2-[(tert-butoxy)-N-methylcarbonylamino]-N-[3-(1-{[4-(4-methoxyphenylthio)phenyl]methyl} (4-piperidyl))-4-methylphenyl]acetamide was dissolved in CH2Cl2 (1.00 mL) and trifluoroacetic acid (0.160 mL) was added to the stirred solution. Stirring was continued for 10 min then the reaction mixture was concentrated in vacuo to give a gum. The crude product was dissolved in saturated NaHCO3 solution (10 mL to pH 10) and extracted with CH2Cl2 (2×10 mL). The combined organic layers were dried over MgSO4 and concentrated in vacuo to give N-[3-(1-{[4-(4-methoxyphenylthio)phenyl]methyl}(4-piperidyl))-4-methylphenyl]2-(methylamino)acetamide (68.6 mg, 99.2% yield) as a yellow solid.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customto give a gum
  3. extractionextracted with CH2Cl2 (2×10 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8a2927c8e01e43a1bbcb07fe2b1bbafa
Source dataset
uspto-grants-2008_02
Patent number
US07329656B2

Reaction notes

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