1,4-Dioxane → HCID 15860087, compound

HRID 1953363Notes

Reaction equation

HRID 1953363 reaction equation
Br.[OH:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[OH:11])[CH2:6][NH2:7].[O:12]1[CH2:17][CH2:16][O:15][CH2:14]C1.[C:18]([O-:21])(O)=O.[Na+]>O>[OH:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[OH:11])[CH2:6][NH:7][C:18](=[O:21])/[CH:9]=[CH:8]/[C:5]1[CH:4]=[CH:3][C:17]([OH:12])=[C:16]([O:15][CH3:14])[CH:6]=1

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 133435624-(Aminomethyl)benzene-1,2-diol--hydrogen bromide (1/1)

Product 1

HCID 15860087HCID 15860087, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

N-succinimidyl ferulate (503 mg, 1.73 mmol) and 3,4-dihydroxybenzylamine hydrobromide (402 mg, 1.83 mmol) were dissolved in water (10 ml) and 1,4-dioxane (10 ml) under nitrogen. After NaHCO3 (160 mg, 1.90 mmol) had been added, the solution was stirred for 2.5-3 h at about 70° C. and left to cool. The mixture was extracted with ethyl acetate, the combined organic phases were washed with hydrochloric acid (10%), water and saturated aqueous NaCl solution, dried over Na2SO4 and filtered, and the filtrate was evaporated under reduced pressure and the residue was purified by chromatography on silica gel. Yield: 540 mg (99%); 1H-NMR (400MHz, CDCl3): δ=7.55 (1H, d, 15.5 Hz), 7.02 (1H, dd, 8.2 Hz, 1.9 Hz), 6.93 (1H, s, 1.9 Hz), 6.89 (1H, d, 8.3 Hz), 6.88 (1H, d, 2Hz), 6.82 (1H, d, 8.1 Hz), 8.72 (1H, dd, 8.1 Hz, 2.0 Hz), 6.51 (1H, s), 6.21 (1H, d, 15.5 Hz), 5.82 (1H, t, 5.8 Hz) 5.79 (1H, s), 5.45 (1H, s), 4.45 (2H, d, 5.8 Hz), 3.90 (3H, s) ppm; 13C-NMR (100 MHz, CDCl3): δ=165.1, 148.2, 147.8, 145.1, 144.1, 139.0, 130.3, 126.4, 121.4, 119.0, 118.3, 115.6, 115.3, 115.0, 110.8, 55.5, 41.9 ppm, MS (EI): m/z=315.1 (100%), 178.1 (66%), 177.1 (84%), 150.1 (36%), 147.0 (22%), 145.1 (46%), 138.1 (83%), 117.1 (24%), 89.0 (24%), 77.1 (22%).

Workup

  1. waitleft
  2. temperatureto cool
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe combined organic phases were washed with hydrochloric acid (10%), water and saturated aqueous NaCl solution
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe filtrate was evaporated under reduced pressure
  8. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-b6a0b17650fc4dc8a02f5b26ab7be1ab
Source dataset
uspto-grants-2000_09
Patent number
US06117365

Reaction notes

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