Trifluoroacetic acid → HCID 90412579, compound

HRID 1522034Notes

Reaction equation

HRID 1522034 reaction equation
[F:1][C:2]1[C:3]([C:27]2[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=2[O:34][CH3:35])=[C:4]2[CH:10]=[C:9]([C:11]3[CH2:26][CH:14]4[CH2:15][N:16]([CH2:18][C:19]([O:21]C(C)(C)C)=[O:20])[CH2:17][CH:13]4[CH:12]=3)[NH:8][C:5]2=[N:6][CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[F:1][C:2]1[C:3]([C:27]2[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=2[O:34][CH3:35])=[C:4]2[CH:10]=[C:9]([C:11]3[CH2:26][CH:14]4[CH2:15][N:16]([CH2:18][C:19]([OH:21])=[O:20])[CH2:17][CH:13]4[CH:12]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90412318HCID 90412318, compound

Product 1

HCID 90412579HCID 90412579, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 293A (0.685 g, 1.423 mmol) and trifluoroacetic acid (2.74 mL, 35.6 mmol) in dichloromethane (12 mL) was stirred for 18 hours. The mixture was concentrated and the residue was dissolved in 5 mL dichloromethane and treated with 8 mL 2M hydrogen chloride in ether. The suspension was sonicated, diluted with ether, and stirred for 1 hour. The solid was filtered, washed with ether and vacuum oven-dried to give the title compound as a hydrochloride salt. MS (trifluoroacetic acid salt via HPLC) (ESI+) m/z 426.2 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue was dissolved in 5 mL dichloromethane
  3. additiontreated with 8 mL 2M hydrogen chloride in ether
  4. customThe suspension was sonicated
  5. additiondiluted with ether
  6. filtrationThe solid was filtered
  7. washwashed with ether and vacuum
  8. customoven-dried

Sources & evidence

ORD record
ord-2039bb5f62574cfc9bbb9c3a85775b47
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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