Trifluoroacetic acid → HCID 44183931, compound

HRID 451314Notes

Reaction equation

HRID 451314 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([C@@H:18]2[CH2:24][CH2:23][C@@H:22]3[CH2:25][N:19]2[C:20](=[O:31])[N:21]3[O:26][S:27]([OH:30])(=[O:29])=[O:28])=[O:17])=[CH:11][CH:10]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:16]([C@@H:18]2[CH2:24][CH2:23][C@@H:22]3[CH2:25][N:19]2[C:20](=[O:31])[N:21]3[O:26][S:27]([OH:30])(=[O:29])=[O:28])=[O:17])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 89687756HCID 89687756, compound

Product 1

HCID 44183931HCID 44183931, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of the product of step 3 (34.8 mg, 0.074 mmol) in dry dichloromethane (3 mL) at 0° C. under nitrogen was added trifluoroacetic acid (1.0 mL, 13 mmol). All solids dissolved immediately upon addition of trifluoroacetic acid. the solution was stirred for 1.5 ours at which time LC-MS analysis showed reaction complete. The reaction was concentrated under vacuum and the residue was triturated with ether to remove excess trifluoroacetic acid and organic impurities. The resulting sticky solid was dried under vacuum and stored in the freezer overnight. The crude product was purified by HPLC on a Phenomenex Synergi Polar-RP 80A column to afford the impure title compound as a white solid after lyophilization. The solid was triturated with acetonitrile (3×) to afford the pure title compound as a white solid. LC-MS (negative ionization) m/e 369 (M−H); LC-MS (positive ionization) m/e 354 (M+H—NH3); 1H NMR (600 MHz, D2O; unreferenced) (δ, ppm) 7.53 (2H, d, J=8.5 Hz), 7.46 (2H, d, J=8.5 Hz), 4.23 (2H, br s), 4.11 (2H, s), 3.39 (1H, d, 3=12 Hz), 3.18 (1H, d, J=12 Hz), 2.27-2.31 (1H, m), 2.09-2.14 (1H, m), 1.90-2.00 (1H, m), 1.813-1.89 (1H, m).

Workup

  1. customreaction complete
  2. concentrationThe reaction was concentrated under vacuum
  3. customthe residue was triturated with ether
  4. customto remove excess trifluoroacetic acid and organic impurities
  5. customThe resulting sticky solid was dried under vacuum
  6. customstored in the freezer overnight
  7. customThe crude product was purified by HPLC on a Phenomenex Synergi Polar-RP 80A column

Sources & evidence

ORD record
ord-523ff6a3a61e483b9cdc4b0b1f0d5eb9
Source dataset
uspto-grants-2013_07
Patent number
US08487093B2

Reaction notes

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