Trifluoroacetic acid → HCID 58002585, compound

HRID 1643014Notes

Reaction equation

HRID 1643014 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]=[C:11]([CH:13]3[CH2:18][CH:17]([C:19]4[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=4)[CH2:16][N:15]([C:30](=[O:42])[C:31]([NH:34]C(=O)OC(C)(C)C)([CH3:33])[CH3:32])[CH2:14]3)[O:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.FC(F)(F)C(O)=O>ClCCl.C(OCC)(=O)C>[NH2:34][C:31]([CH3:33])([CH3:32])[C:30]([N:15]1[CH2:16][CH:17]([C:19]2[CH:20]=[CH:21][C:22]([O:25][C:26]([F:28])([F:29])[F:27])=[CH:23][CH:24]=2)[CH2:18][CH:13]([C:11]2[O:10][N:9]=[C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)[N:12]=2)[CH2:14]1)=[O:42]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58002628HCID 58002628, compound

Product 1

HCID 58002585HCID 58002585, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

110 mg (0.186 mmol) of the compound from Example 188A were initially charged in 1.4 ml of dichloromethane, and 143 μl (212 mg, 1.87 mmol) of trifluoroacetic acid were added. The reaction mixture was stirred at RT for 12 h, and then taken up in ethyl acetate and washed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution. The organic phase was dried over sodium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by preparative HPLC. Yield: 48 mg (53% of theory)

Workup

  1. washwashed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  2. dry with materialThe organic phase was dried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-a2c0e7c850314c2b865860718c646a0f
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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