Hydrogen Bromide → HCID 12021101, compound

HRID 1016305Notes

Reaction equation

HRID 1016305 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12](=[O:16])[C:11]3[C:6]4=[C:7]([C:19](=[O:29])[C:20]([CH2:22][C:23]5[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=5)=[CH:21][N:5]4[C:4]=2[CH:3]=1)[CH:8]=[C:9]([O:17]C)[CH:10]=3.Br.[OH-].[Na+]>C(O)(=O)C>[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12](=[O:16])[C:11]3[C:6]4=[C:7]([C:19](=[O:29])[C:20]([CH2:22][C:23]5[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=5)=[CH:21][N:5]4[C:4]=2[CH:3]=1)[CH:8]=[C:9]([OH:17])[CH:10]=3

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 12021100HCID 12021100, compound

Product 1

HCID 12021101HCID 12021101, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The compound (100 mg) obtained in Example 32 was suspended in acetic acid (3 mL) and to the suspension was added 47% hydrobromic acid (3 mL). The mixture was heated under reflux for 20 hours. After allowing to cool, the mixture was alkalized with 6N-sodium hydroxide and extracted with ethyl acetate. The ethyl acetate layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate) to obtain the title compound (69 mg; 71%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 20 hours
  3. temperatureto cool
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-862932c7f5764f8b91d23b0dc5d859d3
Source dataset
uspto-grants-2002_11
Patent number
US06476021B1

Reaction notes

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