Potassium Hydroxide → HCID 9968310, compound

HRID 2306085Notes

Reaction equation

HRID 2306085 reaction equation
[CH2:1]([O:8][N:9]1[C@@H:13]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=2)[CH2:12][NH:11]C1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>C(O)C.O>[CH2:1]([O:8][NH:9][C@@H:13]([CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=1)[CH2:12][NH2:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14797Potassium Hydroxide2×HCID 10110107HCID 10110107, compound

Product 1

HCID 9968310HCID 9968310, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of Example 3F in ethanol (300 mL) was treated with a solution of 30% (w/w) KOH in water (100 mL), heated to reflux, stirred for 8 hours, treated with additional 30% KOH in water (5 mL), stirred for 40 minutes, cooled to room temperature, concentrated to a slurry, and extracted with toluene. The extract was washed with 1M NaOH and brine, dried (Na2SO4), filtered, and concentrated to provide 48.6 g of the desired product. 1H NMR (300 MHz, DMSO-d6) δ7.45 (m, 2H), 7.33 (m, 5H), 6.90 (m, 2H), 6.67 (d, 1H, J=5 Hz), 4.63 (s, 2H), 3.95 (m, 2H), 3.08 (m, 1H), 2.73 (m, 1H), 2.62 (m, 1H), 1.40 (br s, 2H).

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. stirringstirred for 40 minutes
  4. concentrationconcentrated to a slurry
  5. extractionextracted with toluene
  6. washThe extract was washed with 1M NaOH and brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-ff57a7571b844bd39cc6ae5cf760ceb3
Source dataset
uspto-grants-2002_08
Patent number
US06441189B1

Reaction notes

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