Trifluoroacetic acid → HCID 67414877, compound

HRID 716108Notes

Reaction equation

HRID 716108 reaction equation
C(OC(=O)[NH:7][CH:8]([C:12]([N:14]1[CH2:18][CH2:17][CH2:16][CH:15]1[CH2:19][C:20]1[C:28]2[CH:27]=[CH:26][C:25]([F:29])=[CH:24][C:23]=2[N:22]2[CH2:30][CH2:31][N:32]3[C:40]4[C:35](=[CH:36][CH:37]=[C:38]([F:41])[CH:39]=4)[C:34]([CH2:42][CH:43]4[CH2:47][CH2:46][CH2:45][N:44]4[C:48](=[O:61])[CH:49]([NH:53]C(OC(C)(C)C)=O)[CH:50]([CH3:52])[CH3:51])=[C:33]3[C:21]=12)=[O:13])[CH:9]([CH3:11])[CH3:10])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][CH:8]([CH:9]([CH3:11])[CH3:10])[C:12]([N:14]1[CH2:18][CH2:17][CH2:16][CH:15]1[CH2:19][C:20]1[C:28]2[CH:27]=[CH:26][C:25]([F:29])=[CH:24][C:23]=2[N:22]2[CH2:30][CH2:31][N:32]3[C:40]4[C:35](=[CH:36][CH:37]=[C:38]([F:41])[CH:39]=4)[C:34]([CH2:42][CH:43]4[CH2:47][CH2:46][CH2:45][N:44]4[C:48](=[O:61])[CH:49]([NH2:53])[CH:50]([CH3:52])[CH3:51])=[C:33]3[C:21]=12)=[O:13]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67413906HCID 67413906, compound

Product 1

HCID 67414877HCID 67414877, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution containing 30 (1.09 g, 1.27 mmol) in DCM (20 mL) was cooled to 0° C. TFA (4 mL) was added via pipette and the reaction was monitored until TLC analysis revealed complete consumption of 30 (˜2 h). TLC analysis, 10% MeOH/DCM, Rf(30)=0.5; Rf(31)=0.4. The solvent was removed on a rotary evaporator and the residue was dissolved in EtOAc. The EtOAc solution was washed twice with saturated aqueous NaHCO3 and once with brine. The combined aqueous washes were back-extracted with EtOAc and the organic extracts were dried over anhydrous Na2SO4, filtered, and concentrated to afford 0.83 g (quant.) of 31 as a yellow solid which was used without further purification. 1H NMR (CDCl3, 300 MHz) δ8.09 (dd, J=5.1, 8.7 Hz, 1H), 6.97 (m, 2H), 4.52 (m, 1H), 4.50 (d, J=8.7 Hz, 1H), 4.11 (m, 1H), 3.71 (br d, J=11.1 Hz, 1H), 3.51-3.32 (m, 2H), 2.74 (app t, J=12.6 Hz, 1H), 2.30 (br s, 4H), 1.92 (m, 1H), 1.68 (m, 2H), 1.41 (m, 1H), 1.03 (m, 6H) ppm. 13C NMR (CDCl3, 75 MHz) δ174.3, 171.4, 160.6 (d, JC-F=232.5 Hz), 136.8 (d, JC-F=7.5 Hz), 127.4 (d, JC-F=3.7 Hz), 125.0, 122.4 (d, JC-F=7.5 Hz), 109.6, 108.7 (d, JC-F=22.5 Hz), 95.2 (d, JC-F=22.5 Hz), 58.0, 47.3, 41.9, 30.0, 28.5, 28.5, 24.1, 19.9, 17.6 ppm.

Workup

  1. customconsumption of 30 (˜2 h)
  2. customThe solvent was removed on a rotary evaporator
  3. dissolutionthe residue was dissolved in EtOAc
  4. washThe EtOAc solution was washed twice with saturated aqueous NaHCO3 and once with brine
  5. extractionThe combined aqueous washes were back-extracted with EtOAc
  6. dry with materialthe organic extracts were dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c23e47fecaf347f0a6b4f03d1b938e89
Source dataset
uspto-grants-2015_11
Patent number
US09187490B2

Reaction notes

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