Water → HCID 86587860, compound

HRID 1374782Notes

Reaction equation

HRID 1374782 reaction equation
BrNC(=[O:5])C.[OH:6][C@H:7]1[CH2:29][CH2:28][C@@:27]2([CH3:30])[C:9](=[CH:10][CH2:11][C@@H:12]3[C@@H:26]2[CH2:25][C@@H:24]([OH:31])[C@@:23]2([CH3:32])[C:13]3=[CH:14][CH2:15][C@@H:16]2[C:17]2([O:22][CH2:21][CH2:20][O:19]2)[CH3:18])[CH2:8]1.O.S([O-])([O-])=O.[Na+].[Na+]>CC(C)=O.C(O)(=O)C>[OH:6][C@H:7]1[CH2:29][CH2:28][C@@:27]2([CH3:30])[C:9]3([O:5][CH:10]3[CH2:11][C@@H:12]3[C@@H:26]2[CH2:25][C@@H:24]([OH:31])[C@@:23]2([CH3:32])[C:13]3=[CH:14][CH2:15][C@@H:16]2[C:17]2([O:19][CH2:20][CH2:21][O:22]2)[CH3:18])[CH2:8]1

Participants

7

Reactant 4

HCID 962WaterHCID 4353N-BromoacetamideHCID 24437Sodium SulfiteHCID 68808232HCID 68808232, compound

Product 1

HCID 86587860HCID 86587860, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 180AcetoneSolvent

Procedure

N-Bromoacetamide (211 mg, 1.5 mmol) is added to a stirred solution of the 5,14-diene (23) (500 mg, 1.34 mmol) in acetone (100 ml), acetic acid (2.5 ml), and water (5 ml) at 0° C. After 15 min sodium sulphite (5% soln, 50 ml) is added to the reaction mixture. The acetone is evaporated, and the aqueous layer extracted with dichloromethane (3×50 ml). The organic layer is dried (MgSO4), filtered and evaporated. Pyridine (1 ml) is added to the product, and stirred for 0.5 h. Dichloromethane (100 ml) is then added to the reaction mixture, and the dichloromethane is washed with citric acid (5% soln, 3×100 ml), saturated sodium bicarbonate (50 ml), and water (50 ml). The organic layer is dried (MgSO4), filtered and evaporated to give the mixture of 14,15- and 5,6-epoxides (360 mg, 69%) as a white foam. The mixture of epoxides could not be separated by silica gel column chromatography.

Workup

  1. addition50 ml) is added to the reaction mixture
  2. customThe acetone is evaporated
  3. extractionthe aqueous layer extracted with dichloromethane (3×50 ml)
  4. dry with materialThe organic layer is dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. additionPyridine (1 ml) is added to the product
  8. additionDichloromethane (100 ml) is then added to the reaction mixture
  9. washthe dichloromethane is washed with citric acid (5% soln, 3×100 ml), saturated sodium bicarbonate (50 ml), and water (50 ml)
  10. dry with materialThe organic layer is dried (MgSO4)
  11. filtrationfiltered
  12. customevaporated
  13. customto give
  14. custombe separated by silica gel column chromatography

Sources & evidence

ORD record
ord-7aaea268bc1d45999eb304a39ffb0e3a
Source dataset
uspto-grants-2007_01
Patent number
US07166611B2

Reaction notes

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