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Methyl chloroformate → (E,E)-N-[3-[3-(3-thienyl)phenyl]-2-propenyl]-(N'-ethyl-6,6-dimethyl-2-hepten-4-ynylamino)acetamide

HRID 1464746
Notes
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Reaction equation

HRID 1464746 reaction equation
Cl.[CH2:2]([N:4]([CH2:9]/[CH:10]=[CH:11]/[C:12]#[C:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:5][C:6]([OH:8])=O)[CH3:3].ClC(OC)=O.C(N(CC)CC)C.[S:30]1[CH:34]=[CH:33][C:32]([C:35]2[CH:36]=[C:37](/[CH:41]=[CH:42]/[CH2:43][NH2:44])[CH:38]=[CH:39][CH:40]=2)=[CH:31]1>C(Cl)Cl>[S:30]1[CH:34]=[CH:33][C:32]([C:35]2[CH:36]=[C:37](/[CH:41]=[CH:42]/[CH2:43][NH:44][C:6](=[O:8])[CH2:5][N:4]([CH2:9]/[CH:10]=[CH:11]/[C:12]#[C:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:2][CH3:3])[CH:38]=[CH:39][CH:40]=2)=[CH:31]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 19917024(E)-N-ethyl-N-(6,6-dimethyl-2-hepten-4-ynyl)glycine hydrochlorideHCID 19917058(E)-3-[3-(3-thienyl)phenyl]-2-propenylamine

Product 1

HCID 19086968(E,E)-N-[3-[3-(3-thienyl)phenyl]-2-propenyl]-(N'-ethyl-6,6-dimethyl-2-hepten-4-ynylamino)acetamideYield 17%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

100 mg of (E)-N-ethyl-N-(6,6-dimethyl-2-hepten-4-ynyl)glycine hydrochloride was dissolved in 10 ml of methylene chloride, and 34 μl of methyl chloroformate and 0.1 ml of triethylamine were added under ice cooling. The mixture was stirred for 30 minutes, and a methylene chloride solution(5 ml) of 90 mg of (E)-3-[3-(3-thienyl)phenyl]-2-propenylamine was added, then the mixture was stirred at room temperature for 2 hours. The solvent was evaporated under reduced pressure, and ethyl acetate and water were added to the residue to extract it. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The desiccant was separated by filtration and the solvent was evaporated under reduced pressure. The residue was purified by medium-pressure liquid chromatography [silica gel column, hexane→hexane/ethyl acetate=5/1] to give 24 mg (yield 17%) of the captioned compound as a pale yellow oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. customThe solvent was evaporated under reduced pressure, and ethyl acetate and water
  3. additionwere added to the residue
  4. extractionto extract it
  5. customThe organic layer was separated
  6. washwashed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe desiccant was separated by filtration
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was purified by medium-pressure liquid chromatography [silica gel column, hexane→hexane/ethyl acetate=5/1]

Sources & evidence

ORD record
ord-2fbca4abbfff41a98ede41c720ba3e2c
Source dataset
uspto-grants-1994_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05306728

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes