Acetic Acid → HCID 19744681, compound

HRID 2254410Notes

Reaction equation

HRID 2254410 reaction equation
[N+:1]([CH2:3][C:4]([O:6][CH3:7])=[O:5])#[C-:2].CCCCCCC=CCCC.[O:19]1[CH2:23]C[CH2:21][CH2:20]1.[CH3:24][C:25]([CH3:51])([CH3:50])[C:26]#[C:27]/[CH:28]=[CH:29]/[CH2:30][N:31]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[C:44]([CH:48]=O)[CH:43]=2)[CH:35]=1)[CH3:32].C(O)(=[O:54])C>>[CH3:24][C:25]([CH3:51])([CH3:50])[C:26]#[C:27]/[CH:28]=[CH:29]/[CH2:30][N:31]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[C:44]([C:48]3[C:21]([C:20]([O:19][CH3:23])=[O:54])=[CH:2][NH:1][C:3]=3[C:4]([O:6][CH3:7])=[O:5])[CH:43]=2)[CH:35]=1)[CH3:32]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 8028Tetrahydrofuran2×HCID 136496Undec-4-eneHCID 547815Methyl isocyanoacetateHCID 19744731HCID 19744731, compound

Product 1

HCID 19744681HCID 19744681, compoundYield 20%

Procedure

Methyl isocyanoacetate (280 microliters) and 400 microliters of 1,8-diazabicyclo5.4.0]undeca-7-ene (DBU) were added to 20 ml of tetrahydrofuran, and with stirring at 45° to 50° C., a tetrahydrofuran solution (5 ml) of 500 mg of (E)-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-methyl-3-(3-formylbenzyloxy)benzylamine was added, and the mixture was stirred at the above temperature for 5 hours. The reaction mixture was allowed to cool and neutralized with acetic acid. The solvent was evaporated under reduced pressure and ethyl acetate and water was added to the residue to extract it. The organic layer was separated, dried over anhydrous magnesium sulfate. The desiccant was separated by filtration, and the solvent was evaporated. Then, the residue was purified by silica gel column chromatography [Wakogel C-200, 30 g, eluting solvent: hexane/ethyl acetate:5/1] to give 140 mg (yield 20%) of (E)-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-methyl-3-[3-(2,4-dimethoxycarbonyl-3-pyrrolyl)benzyloxy)benzylamine as a pale yellow oil.

Workup

  1. stirringthe mixture was stirred at the above temperature for 5 hours
  2. temperatureto cool
  3. customThe solvent was evaporated under reduced pressure and ethyl acetate and water
  4. additionwas added to the residue
  5. extractionto extract it
  6. customThe organic layer was separated
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe desiccant was separated by filtration
  9. customthe solvent was evaporated
  10. customThen, the residue was purified by silica gel column chromatography [Wakogel C-200, 30 g, eluting solvent: hexane/ethyl acetate:5/1]

Sources & evidence

ORD record
ord-4c9d461951a043a7a10217eda3fd6e6c
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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