Hydrogen Bromide → HCID 71062920, compound

HRID 1506793Notes

Reaction equation

HRID 1506793 reaction equation
Br.[CH2:2]([C:4]1([CH2:17][C:18]([O:20]CC)=[O:19])[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:14]C)[CH:10]=2)[C:5]1=[O:16])[CH3:3]>O>[CH2:2]([C:4]1([CH2:17][C:18]([OH:20])=[O:19])[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:14])[CH:10]=2)[C:5]1=[O:16])[CH3:3]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 71062915HCID 71062915, compound

Product 1

HCID 71062920HCID 71062920, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Aqueous HBr (70 mL) was added to 4A (7 g, 24.13 mmol) and the reaction mixture was refluxed for 4 h. The reaction mixture was then brought to room temperature, diluted with water and extracted with ethyl acetate (2×100 mL). The organic layers were dried over sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The crude product was purified using flash chromatography using 40% ethyl acetate in hexanes to afford the title compound (5 g, 83.6%) as a solid. 1H NMR (400 MHz, DMSO-d6): δ 12.0 (s, 1H), 10.3 (s, 1H), 7.8 (d, J=8.4 Hz, 1H), 6.7 (d, J=7.4 Hz, 1H), 6.6 (s, 1H), 3.0 (m, 1H), 2.7 (m, 2H), 2.4 (m, 2H), 1.9 (m, 1H), 1.7-1.5 (m, 2H), 0.9 (t, J=7.6 Hz, 3H). ESI-MS m/z=247 (M−H)−.

Workup

  1. temperaturethe reaction mixture was refluxed for 4 h
  2. customwas then brought to room temperature
  3. extractionextracted with ethyl acetate (2×100 mL)
  4. dry with materialThe organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe crude product was purified

Sources & evidence

ORD record
ord-19c8dd277ffe4c6b8f64cec11c6a6b06
Source dataset
uspto-grants-2015_12
Patent number
US09221766B2

Reaction notes

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