Trifluoroacetic acid → HCID 178512772, compound

HRID 1050932Notes

Reaction equation

HRID 1050932 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][NH:23][C:24]([NH:33]C(OC(C)(C)C)=O)=[N:25]C(OC(C)(C)C)=O)=[CH:18][C:17]=2[Br:41])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[F:42][C:43]([F:48])([F:47])[C:44]([OH:46])=[O:45]>C(Cl)Cl>[F:42][C:43]([F:48])([F:47])[C:44]([OH:46])=[O:45].[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][NH:23][C:24]([NH2:33])=[NH:25])=[CH:18][C:17]=2[Br:41])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178454249HCID 178454249, compound

Product 1

HCID 178512772HCID 178512772, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 25 mL round bottom flask was charged with Compound 4 (3.00 g, 4.15 mmol) then CH2Cl2 (6 mL), and the resulting suspension stirred until complete dissolution was observed. Trifluoroacetic acid (6 mL, 78.3 mmol) was then added and the mixture stirred an additional 4 h. All volatiles were then removed, and the residue treated with EtOAc (20 mL). The resulting mixture was stirred at room temperature for 3 h, during which time a white solid precipitated. The solids were collected on a sintered glass funnel of medium porosity then exhaustively washed with EtOAc (20 mL) and dried to constant weight (2.5 g, 95%). 1H NMR (400 MHz, DMSO-d6) δ 7.54 (m, 4H), 7.4 (d, 1H), 7.15 (m, 1H), 6.9 (d, 1H), 4.15 (m, 4H), 3.86 (m, 2H), 1.92 (m, 2H).

Workup

  1. customAll volatiles were then removed
  2. additionthe residue treated with EtOAc (20 mL)
  3. stirringThe resulting mixture was stirred at room temperature for 3 h, during which time a white solid
  4. customprecipitated
  5. customThe solids were collected on a sintered glass funnel of medium porosity
  6. washthen exhaustively washed with EtOAc (20 mL)
  7. customdried to constant weight (2.5 g, 95%)

Sources & evidence

ORD record
ord-21ad547a11494405af662f761c8e3226
Source dataset
uspto-grants-2016_07
Patent number
US09388125B2

Reaction notes

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