Trifluoroacetic acid → HCID 57810638, compound

HRID 2106083Notes

Reaction equation

HRID 2106083 reaction equation
C(OC([NH:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH:13]([C:16]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)=[O:17])[CH2:12][CH2:11]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl.CO>[NH2:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH:13]([C:16]([NH:18][CH2:19][C:20]2[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=2)=[O:17])[CH2:12][CH2:11]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70984852HCID 70984852, compound

Product 1

HCID 57810638HCID 57810638, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

5.5 g of the (4-{[(tert-butoxy)carbonylamino]methyl}cyclohexyl)-N-[(4-methylphenyl)methyl]carboxamide prepared in Example 5A was dissolved in 500 ml of CH2Cl2. 50 ml of trifluoroacetic acid (TFA) was added to the solution and the reaction mixture stirred at room temperature overnight. The volatile components of the reaction mixture were evaporated off leaving a colorless oil which was then dissolved in 500 ml of methanol. 1 Tbs of Bio-Rad AG 1-X8 resin (20-50 mesh) was added and the solution shaken for 48 hours. Additional resin was added until the pH was slightly basic. The resin was then removed by filtration and the methanol evaporated off to give the product [4-(aminomethyl)cyclohexyl]-N-[(4-methylphenyl)methyl]carboxamide.

Workup

  1. customThe volatile components of the reaction mixture were evaporated off
  2. customleaving a colorless oil which
  3. additionresin (20-50 mesh) was added
  4. stirringthe solution shaken for 48 hours
  5. additionAdditional resin was added until the pH
  6. customThe resin was then removed by filtration
  7. customthe methanol evaporated off

Sources & evidence

ORD record
ord-92e69d297ba34f1cb16ba6d682368fea
Source dataset
uspto-grants-2009_08
Patent number
US07579504B2

Reaction notes

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