Trifluoroacetic acid → HCID 16075044, compound

HRID 1015668Notes

Reaction equation

HRID 1015668 reaction equation
C([O:5][C:6]([C:8]1[S:9][C:10]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:11][C:12]=1[C:13](=[O:26])[N:14]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=1[Cl:25])[CH:15]([CH3:17])[CH3:16])=[O:7])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:25][C:19]1[CH:20]=[C:21]([Cl:24])[CH:22]=[CH:23][C:18]=1[N:14]([CH:15]([CH3:17])[CH3:16])[C:13]([C:12]1[CH:11]=[C:10]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[S:9][C:8]=1[C:6]([OH:7])=[O:5])=[O:26]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58390745HCID 58390745, compound

Product 1

HCID 16075044HCID 16075044, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-[(2,4-Dichloro-phenyl)-isopropyl-carbamoyl]-5-phenyl-thiophene-2-carboxylic acid tert-butyl ester (37 mg, 0.08 mmol) in CH2Cl2 (0.2 ml) at room temperature, under nitrogen was treated with trifluoroacetic acid (0.8 ml). After 1 h the reaction was concentrated the residue was taken into EtOAc and washed sequentially with 2N HCl (2×15 ml), water, brine dried and evaporated to a foam (33 mg). The foam was redissolved in EtOAc and above acidic wash was repeated to yield 27 mg (84%) of 3-[(2,4-Dichloro-phenyl)-isopropyl-carbamoyl]-5-phenyl-thiophene-2-carboxylic acid compound as pale brown foam. NMR 1H: (CD3OD; 400 MHz) 7.57-7.55 (m, 2H); 7.49-7.36 (m, 6H), 7.30-7.27 (m, 1H); 4.89 (quint, J=6.73 Hz, 1H); 1.42 (d, J=6.73 Hz, 3H); 1.12 (d, J=6.73 Hz, 3H).

Workup

  1. concentrationAfter 1 h the reaction was concentrated the residue
  2. washwashed sequentially with 2N HCl (2×15 ml), water, brine
  3. customdried
  4. customevaporated to a foam (33 mg)
  5. dissolutionThe foam was redissolved in EtOAc
  6. washabove acidic wash

Sources & evidence

ORD record
ord-695d0c41085b4ed4be2a3d98c987bdf5
Source dataset
uspto-grants-2011_07
Patent number
US07985769B2

Reaction notes

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