Trifluoroacetic acid → HCID 67148496, compound

HRID 1054001Notes

Reaction equation

HRID 1054001 reaction equation
C(OC(=O)[NH:7][CH:8]([C:10](=[O:34])[NH:11][CH:12]([C:16]([N:18]1[CH2:22][CH2:21][CH2:20][CH:19]1[CH2:23][C:24]1[C:28]2[CH:29]=[C:30]([OH:33])[CH:31]=[CH:32][C:27]=2[O:26][CH:25]=1)=[O:17])[CH:13]([CH3:15])[CH3:14])[CH3:9])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][CH:8]([CH3:9])[C:10]([NH:11][CH:12]([C:16]([N:18]1[CH2:22][CH2:21][CH2:20][CH:19]1[CH2:23][C:24]1[C:28]2[CH:29]=[C:30]([OH:33])[CH:31]=[CH:32][C:27]=2[O:26][CH:25]=1)=[O:17])[CH:13]([CH3:15])[CH3:14])=[O:34]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67148251HCID 67148251, compound

Product 1

HCID 67148496HCID 67148496, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 31 (0.04 g, 0.082 mmol) in DCM (5 mL) was added TFA (1 mL) at ambient temperature. After 1 h, the solvent was removed under reduced pressure. The residue was dissolved in EtOAc and washed with aqueous NaHCO3, brine, dried over anhydrous Na2SO4, filtered and concentrated. The crude product was purified by flash silica gel chromatography (10% MeOH/DCM) to afford 0.011 g (37%) of 32 as a white solid. 1H NMR (CDCl3, 300 MHz) 88.54 (d, 1H); 7.37 (s, 1H); 7.31 (d, 1H); 7.09 (d, 1H); 6.83 (dd, 1H); 4.64 (t, 1H); 4.56-4.51 (m, 1H); 4.09-3.93 (m, 2H); 3.73-3.65 (m, 1H); 3.36 (dd, 1H); 2.35 (t, 1H); 2.19-1.94 (m, 3H); 1.77-1.69 (m, 2H); 1.33 (d, 2H); 1.25-1.19 (m, 1H); 1.04-1.00 (m, 5H); 0.94 (t, 1H) ppm.

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with aqueous NaHCO3, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by flash silica gel chromatography (10% MeOH/DCM)

Sources & evidence

ORD record
ord-bfb3ca57c524492b8c8cf4b6dbcbc8f0
Source dataset
uspto-grants-2016_07
Patent number
US09394249B2

Reaction notes

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