1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 72529809, compound

HRID 1685820Notes

Reaction equation

HRID 1685820 reaction equation
Cl[CH:2]([CH:16]1[CH2:20][CH2:19][CH2:18][S:17]1(=[O:22])=[O:21])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][CH:4]=1.N12CCCN=C1CCCCC2>C1C=CC=CC=1>[O:21]=[S:17]1(=[O:22])[CH2:18][CH2:19][CH2:20][C:16]1=[CH:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 59202189HCID 59202189, compound

Product 1

HCID 72529809HCID 72529809, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Ethyl 2-{4-[chloro-(1,1-dioxotetrahydro-1λ6-thiophen-2-yl)methyl]phenyl} propionate (420 mg) obtained in Example 39 was dissolved in benzene (7.0 ml), and to the solution was added 1,8-diazabicyclo[5.4.0]undec-7-ene (0.45 ml), and the mixture was stirred for 3 hours. The reaction mixture was quenched with water, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over sodium sulfate. The solvent was evaporated under reduced pressure, and then the residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1) to give the title compound (300 mg, 79%).

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-2f507fa98507484aa19a2f545bb37f71
Source dataset
uspto-grants-2012_04
Patent number
US08148421B2

Reaction notes

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