Trifluoroacetic acid → HCID 67305317, compound

HRID 1454990Notes

Reaction equation

HRID 1454990 reaction equation
FC(F)(F)C(O)=O.[C:8]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][CH2:15][C:16]([N:19]2[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]2)([CH3:18])[CH3:17])[CH:9]=1>ClCCl.ClCCCl>[C:8]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][CH2:15][C:16]([N:19]2[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]2)([CH3:18])[CH3:17])[CH:9]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 67306155HCID 67306155, compound

Product 1

HCID 67305317HCID 67305317, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

0.65 ml (8.4 mmol) of trifluoroacetic acid is added to a solution of 0.35 g (0.86 mmol) of 1,1-dimethylethyl 4-(3-biphenyl-3-yl-1,1-dimethylpropyl)piperazine-1-carboxylate, prepared in step 5.3., in 5 ml of dichloromethane. The mixture is stirred for 2 hours and then 0.65 ml of trifluoroacetic acid is added. It is stirred for 2 more hours and then diluted with 10 ml of 1,2-dichloroethane and evaporated to dryness. The residue is taken up in a mixture of 50 ml of dichloromethane and 20 ml of 15% aqueous sodium hydroxide solution. The phases are separated and the aqueous phase is extracted with 2 times 20 ml of dichloromethane. The organic phases are washed with 10 ml of water and then with 20 ml of saturated aqueous sodium chloride solution, dried over sodium sulphate and evaporated, to give 0.25 g (0.81 mmol) of product in the form of a yellow oil.

Workup

  1. customprepared in step 5.3
  2. stirringIt is stirred for 2 more hours
  3. customevaporated to dryness
  4. additionThe residue is taken up in a mixture of 50 ml of dichloromethane and 20 ml of 15% aqueous sodium hydroxide solution
  5. customThe phases are separated
  6. extractionthe aqueous phase is extracted with 2 times 20 ml of dichloromethane
  7. washThe organic phases are washed with 10 ml of water
  8. dry with materialwith 20 ml of saturated aqueous sodium chloride solution, dried over sodium sulphate
  9. customevaporated

Sources & evidence

ORD record
ord-d6398929668e4446a62716a874d75ca0
Source dataset
uspto-grants-2009_01
Patent number
US07482346B2

Reaction notes

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