1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 19434056, compound

HRID 1736023Notes

Reaction equation

HRID 1736023 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][N:6]([S:10]([C:13]1[S:14][CH:15]=[CH:16][C:17]=1[CH:18]1OCCO1)(=[O:12])=[O:11])[CH:7]([CH3:9])[CH3:8])[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+].C1CCN2C(=NCCC2)CC1>CC(C)=O.C(OCC)(=O)C>[CH3:8][CH:7]([N:6]1[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:23])=[CH:18][C:17]2[CH:16]=[CH:15][S:14][C:13]=2[S:10]1(=[O:12])=[O:11])[CH3:9]

Participants

7

Reactant 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 19434043HCID 19434043, compound

Product 1

HCID 19434056HCID 19434056, compoundYield 33.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the product from Step B (36.25 g) and p-toluenesulfonic acid hydrate (2.0 g) in acetone (300 mL) was heated at reflux temperature for 6 h, cooled and a saturated aqueous solution of sodium bicarbonate (100 mL) was added. Acetone was evaporated and the aqueous mixture was extracted with ether (2×100 mL). The combined extracts were dried (MgSO4) and evaporated to give a dark brown oil which was dissolved in ethyl acetate (200 mL). DBU (2 mL) was added to this solution and after 1 h the reaction mixture was washed with 2N HCl and brine, dried (MgSO4), and evaporated to give a solid which was recrystallized from 25% ethyl acetate/hexane to give 9.95 g of product. The mother liquor was chromatographed (silica, 25% ethyl acetate/hexane) to give an additional 3.57 g of product (total 13.52 g, 50%): mp 97°-99° C.

Workup

  1. temperatureat reflux temperature for 6 h
  2. temperaturecooled
  3. customAcetone was evaporated
  4. extractionthe aqueous mixture was extracted with ether (2×100 mL)
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. customevaporated
  7. customto give a dark brown oil which
  8. washwas washed with 2N HCl and brine
  9. dry with materialdried (MgSO4)
  10. customevaporated
  11. customto give a solid which
  12. customwas recrystallized from 25% ethyl acetate/hexane

Sources & evidence

ORD record
ord-ce066128206241a0a0b730297f71027b
Source dataset
uspto-grants-1996_07
Patent number
US05538966

Reaction notes

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