1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 19434131, compound

HRID 1736020Notes

Reaction equation

HRID 1736020 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH2:4][N:5]([S:14]([C:17]1[S:18][CH:19]=[CH:20][C:21]=1[CH:22]=O)(=[O:16])=[O:15])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1.C1CCN2C(=NCCC2)CC1>C(OCC)(=O)C>[CH3:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([N:5]2[C:4]([C:3]([O:2][CH3:1])=[O:24])=[CH:22][C:21]3[CH:20]=[CH:19][S:18][C:17]=3[S:14]2(=[O:16])=[O:15])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 19434003HCID 19434003, compound

Product 1

HCID 19434131HCID 19434131, compoundYield 54.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the product from Step B (3.67 g, 9.95 mmol), DBU (1.0 mL) and molecular sieves (1.5 g) in ethyl acetate (100 mL) was heated at reflux temperature for 4 h, cooled to room temperature, washed with 2N HCl (50 mL) and brine (50 mL), and dried (MgSO4). Evaporation of the solvent provided the desired ester (1.92 g) as an oil which was used without further purification.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 4 h
  3. washwashed with 2N HCl (50 mL) and brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-0fb0409f17544edc889cdb15e960e166
Source dataset
uspto-grants-1996_07
Patent number
US05538966

Reaction notes

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