Trifluoroacetic acid → HCID 86649122, compound

HRID 1471040Notes

Reaction equation

HRID 1471040 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=3)[CH:11]([C:23]3[CH:24]=[CH:25][C:26]([NH:48]CC4C=CC(OC)=CC=4OC)=[C:27]([NH:29][C:30]([C@@H:32]4[CH2:36][CH2:35][CH2:34][N:33]4[C:37](=[O:47])[C@@H:38]([NH:42][C:43](=[O:46])[O:44][CH3:45])[CH:39]([CH3:41])[CH3:40])=[O:31])[CH:28]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:48][C:26]1[CH:25]=[CH:24][C:23]([CH:11]2[CH2:10][CH2:9][CH:8]([C:5]3[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=3)[N:12]2[C:13]2[CH:14]=[CH:15][C:16]([C:19]([CH3:21])([CH3:22])[CH3:20])=[CH:17][CH:18]=2)=[CH:28][C:27]=1[NH:29][C:30]([C@@H:32]1[CH2:36][CH2:35][CH2:34][N:33]1[C:37](=[O:47])[C@@H:38]([NH:42][C:43](=[O:46])[O:44][CH3:45])[CH:39]([CH3:41])[CH3:40])=[O:31]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86649123HCID 86649123, compound

Product 1

HCID 86649122HCID 86649122, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from example 191G (0.65 g, 0.748 mmole) was dissolved in CH2Cl2 (10 mL) then added concentrated trifluoroacetic acid (2 mL, 26 mmole)) and the reaction mixture was stirred 10 minutes. The solvent was removed in vacuo and the residue was re-evaporated twice from CH2Cl2 and once from toluene. The residue was dissolved in EtOAc (100 mL) washed with 10% NaHCO3, dried over anhydrous Na2SO4(s), filtered and solvent removed in vacuo leaving a brown foamy material as the title compound as a mixture of isomers (0.5 g).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was re-evaporated twice from CH2Cl2 and once from toluene
  3. dissolutionThe residue was dissolved in EtOAc (100 mL)
  4. washwashed with 10% NaHCO3
  5. dry with materialdried over anhydrous Na2SO4(s)
  6. filtrationfiltered
  7. customsolvent removed in vacuo

Sources & evidence

ORD record
ord-b65574ae3bc04f01a11886b7df1e1487
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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