Water → HCID 131728914, compound

HRID 551673Notes

Reaction equation

HRID 551673 reaction equation
O.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.[C:16]([O:20][C:21]([NH:23][CH2:24][C@@:25]1([CH2:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:31][C@H:30]2[C@@H:26]1[CH:27]=[C:28]([CH2:32][O:33]CC1C=CC(OC)=CC=1)[CH2:29]2)=[O:22])([CH3:19])([CH3:18])[CH3:17]>C(Cl)Cl>[C:16]([O:20][C:21]([NH:23][CH2:24][C@@:25]1([CH2:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:31][C@H:30]2[C@@H:26]1[CH:27]=[C:28]([CH2:32][OH:33])[CH2:29]2)=[O:22])([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 962WaterHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 131728915HCID 131728915, compound

Product 1

HCID 131728914HCID 131728914, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Water (1.4 mL) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (831 mg, 3.66 mmol) were added to a methylene chloride solution (25 mL) of tert-butyl(±)-[(1R,5R,6R)-6-{[(tert-butoxycarbonyl)amino]methyl}-3-{[(4-methoxybenzyl)oxy]methyl}bicyclo[3.2.0]hept-3-en-6-yl]acetate (1.19 g, 2.44 mmol) with stirring at 0° C. The mixture was stirred at this temperature 0° C. for 1 hour and further stirred at room temperature for 1 hour. Then, the reaction was terminated by the addition of a saturated aqueous solution of sodium bicarbonate, followed by extraction with methylene chloride. The organic layer was washed with water, a saturated aqueous solution of sodium bicarbonate, and saturated saline and dried over anhydrous sodium sulfate. The residue was filtered and concentrated under reduced pressure. Then, the obtained crude product was purified by silica gel column chromatography to obtain the compound of interest as an oil substance (571 mg, 64%).

Workup

  1. stirringThe mixture was stirred at this temperature 0° C. for 1 hour
  2. stirringfurther stirred at room temperature for 1 hour
  3. customThen, the reaction was terminated by the addition of a saturated aqueous solution of sodium bicarbonate
  4. extractionfollowed by extraction with methylene chloride
  5. washThe organic layer was washed with water
  6. dry with materiala saturated aqueous solution of sodium bicarbonate, and saturated saline and dried over anhydrous sodium sulfate
  7. filtrationThe residue was filtered
  8. concentrationconcentrated under reduced pressure
  9. customThen, the obtained crude product
  10. customwas purified by silica gel column chromatography
  11. customto obtain the compound of interest as an oil substance (571 mg, 64%)

Sources & evidence

ORD record
ord-ead38cec8e2d4c88b00e5cf7dee58e87
Source dataset
uspto-grants-2011_05
Patent number
US07947738B2

Reaction notes

Loading…