HCID 68705258, compound → HCID 68707006, compound

HRID 2234198Notes

Reaction equation

HRID 2234198 reaction equation
[BrH:1].Br.[Br:3][C:4]1[CH:9]=[CH:8][C:7]([O:10]C)=[CH:6][C:5]=1[CH2:12][CH2:13][O:14][CH2:15][CH2:16][C:17]([N:19]([CH2:36][CH2:37][N:38]([CH2:41][CH3:42])[CH2:39][CH3:40])[CH2:20][CH2:21][NH:22][CH2:23][CH2:24][C:25]1[C:33]2[S:32][C:31](=[O:34])[NH:30][C:29]=2[C:28]([OH:35])=[CH:27][CH:26]=1)=[O:18]>Br>[BrH:3].[BrH:1].[CH2:41]([N:38]([CH2:39][CH3:40])[CH2:37][CH2:36][N:19]([CH2:20][CH2:21][NH:22][CH2:23][CH2:24][C:25]1[C:33]2[S:32][C:31](=[O:34])[NH:30][C:29]=2[C:28]([OH:35])=[CH:27][CH:26]=1)[C:17](=[O:18])[CH2:16][CH2:15][O:14][CH2:13][CH2:12][C:5]1[CH:4]=[CH:9][CH:8]=[C:7]([OH:10])[CH:6]=1)[CH3:42]

Participants

3

Reactant 1

HCID 68705258HCID 68705258, compound

Product 1

HCID 68707006HCID 68707006, compound

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
100 °C

Procedure

The product from Example 21 part f) was suspended in 48% aq HBr (1 ml) and heated in a microwave at 100° C. for 30 min. The resulting solution was evaporated, azeotroped with ethanol (×2) to give a residue which solidified on standing. The solid was triturated with acetonitrile and the white solid collected by filtration which was further purified by reverse phase HPLC. The desired product fractions were evaporated in vacuo, the residue dissolved in ethanol and conc. Aq. HBr (1 ml) was added. This solution was evaporated in vacuo and the residue azeotroped with ethanol (×5). The resulting solid was triturated with ethanol and collected by filtration to give the title compound as a white solid (10 mg).

Workup

  1. customThe resulting solution was evaporated
  2. customazeotroped with ethanol (×2)
  3. customto give a residue which
  4. customThe solid was triturated with acetonitrile
  5. filtrationthe white solid collected by filtration which
  6. customwas further purified by reverse phase HPLC
  7. customThe desired product fractions were evaporated in vacuo
  8. dissolutionthe residue dissolved in ethanol
  9. additionconc. Aq. HBr (1 ml) was added
  10. customThis solution was evaporated in vacuo
  11. customthe residue azeotroped with ethanol (×5)
  12. customThe resulting solid was triturated with ethanol
  13. filtrationcollected by filtration

Sources & evidence

ORD record
ord-15cde940836843679beb6de04c8b7eb9
Source dataset
uspto-grants-2010_05
Patent number
US07709511B2

Reaction notes

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