Trifluoroacetic acid → HCID 67324135, compound

HRID 2365440Notes

Reaction equation

HRID 2365440 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]2)(=[O:11])=[O:10])=[C:5]([CH3:25])[CH:4]=1)#[N:2].C(O)(C(F)(F)F)=O>ClCCl>[CH3:25][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][C:6]=1[S:9]([N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)(=[O:11])=[O:10])[C:1]#[N:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67323684HCID 67323684, compound2×

Product 1

HCID 67324135HCID 67324135, compoundYield 107.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1,1-dimethylethyl 4-[(4-cyano-2-methylphenyl)sulfonyl]-1-piperazinecarboxylate (may be prepared as described in Intermediate 8; 3.33 g, 9.11 mmol) and TFA (10 ml, 130 mmol) in dry dichloromethane (10 ml) was stirred at rt for 1 h, then concentrated in vacuo, azeotroping with toluene (25 ml) to give a brown oil. This was partitioned between DCM (50 ml) and sat. aq NaHCO3 (50 ml), then the aqueos layer extracted with DCM:EtOH (3:1, 40 ml). The combined organics were passed through a hydrophobic frit and concentrated in vacuo to give the title compound (2.59 g) as a yellow oil. The product became a pale yellow solid on standing.

Workup

  1. concentrationconcentrated in vacuo
  2. customazeotroping with toluene (25 ml)
  3. customto give a brown oil
  4. customThis was partitioned between DCM (50 ml) and sat. aq NaHCO3 (50 ml)
  5. extractionthe aqueos layer extracted with DCM:EtOH (3:1, 40 ml)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8576459bb61c41a29394d5a7f404e1b2
Source dataset
uspto-grants-2014_04
Patent number
US08697703B2

Reaction notes

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