Trifluoroacetic acid → HCID 58447649, compound

HRID 592170Notes

Reaction equation

HRID 592170 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:14][C:15]([O:17]C(C)(C)C)=[O:16])[CH:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][N:11]=[N:10][CH:9]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:14][C:15]([OH:17])=[O:16])[CH:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][N:11]=[N:10][CH:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58447683Tert-butyl 2-(3-methyl-4-(pyridazin-4-yl)phenyl)acetate

Product 1

HCID 58447649HCID 58447649, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The ester 134-2 obtained in step 2 was stirred in DCM (15 ml) with trifluoroacetic acid (TFA, 3 ml) at room temperature overnight. After concentrated by evaporation, the residue was redistributed between ethyl acetate (30 ml) and 5% Na2CO3 aqueous solution (30 ml). The aqueous phase was acidified to pH around 2 with 6 N HCl solution and extracted with ethyl acetate (40 ml×2). The organic extraction was evaporated to give 2-(3-methyl-4-(pyridazin-4-yl)phenyl)acetic acid 134-3 as a solid which is used for reaction without further purification.

Workup

  1. concentrationAfter concentrated by evaporation
  2. extractionextracted with ethyl acetate (40 ml×2)
  3. extractionThe organic extraction
  4. customwas evaporated

Sources & evidence

ORD record
ord-f6efaed5fa13440caa64c0a9b115cfff
Source dataset
uspto-grants-2016_01
Patent number
US09238646B2

Reaction notes

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