1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86748962, compound

HRID 2399245Notes

Reaction equation

HRID 2399245 reaction equation
C(O[CH:5]([C:17]1[N:21]([CH2:22][C:23]2S[C:25]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:27]=2)[C:20]([CH2:32][CH2:33][CH2:34][CH3:35])=[N:19][CH:18]=1)[CH:6]([CH2:11][C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)[C:7]([O:9][CH3:10])=[O:8])(=O)C.[N:36]12CCCN=C1CCCC[CH2:37]2>C1(C)C=CC=CC=1>[CH2:32]([C:20]1[N:21]([CH2:22][C:23]2[CH:27]=[CH:26][C:25]([C:28]([O:30][CH3:31])=[O:29])=[CH:37][N:36]=2)[C:17](/[CH:5]=[C:6](\[CH2:11][C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)/[C:7]([O:9][CH3:10])=[O:8])=[CH:18][N:19]=1)[CH2:33][CH2:34][CH3:35]

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 54451811HCID 54451811, compound

Product 1

HCID 86748962HCID 86748962, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 3-acetoxy-3-[2-n-butyl-1-{(5-carbomethoxy-2-thienyl)methyl}-1H-imidazol-5-yl]-2-(2-thienyl)methylpropanoate (1.99 g, 3.88 mmol) in dry toluene (150 ml) was treated with 17 ml of 1,8-diazabicyclo-[ 5.4.0]undec-7-ene (DBU) and the resulting solution was heated at 80° C. under argon for 1 hour. The solvent was evaporated, the residue triturated with diethyl ether and activated charcoal was added. After filtration, the filtrate was concentrated to give 6.29 g of an oil that was chromatographed over silica gel with hexane/ethyl acetate (1:1) to give 0.43 g (24%) of methyl (E)-3-[2-n-butyl-1-{(5-carbomethoxy-2-thienyl)methyl)-1H-imidazol-5-yl-2-(2-thienyl)methyl-2-propenoate.

Workup

  1. customThe solvent was evaporated
  2. customthe residue triturated with diethyl ether and activated charcoal
  3. additionwas added
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-dba45c833a734f4886a6a5ee0c645989
Source dataset
uspto-grants-1995_09
Patent number
US05447949

Reaction notes

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