1-{[4-Ethoxymethoxy-2-(hex-5-enyl-methyl-carbamoyl)-cyclopentanecarbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester → 17-Ethoxymethoxy-13-methyl-2,14-dioxo-3,13-diaza-tricyclo[13.3.0.0*4,6*]-octadec-7-ene-4-carboxylic acid ethyl ester

HRID 390116Notes

Reaction equation

HRID 390116 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[CH2:18][CH:17]([O:19][CH2:20][O:21][CH2:22][CH3:23])[CH2:16][CH:15]2[C:24](=[O:33])[N:25]([CH2:27][CH2:28][CH2:29][CH2:30][CH:31]=C)[CH3:26])=[O:13])[CH2:8][CH:7]1[CH:9]=C)=[O:5])[CH3:2]>ClC(Cl)C>[CH2:1]([O:3][C:4]([C:6]12[CH2:8][CH:7]1[CH:9]=[CH:31][CH2:30][CH2:29][CH2:28][CH2:27][N:25]([CH3:26])[C:24](=[O:33])[CH:15]1[CH:14]([CH2:18][CH:17]([O:19][CH2:20][O:21][CH2:22][CH3:23])[CH2:16]1)[C:12](=[O:13])[NH:11]2)=[O:5])[CH3:2]

Participants

3

Reactant 1

HCID 668711271-{[4-Ethoxymethoxy-2-(hex-5-enyl-methyl-carbamoyl)-cyclopentanecarbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 6687123617-Ethoxymethoxy-13-methyl-2,14-dioxo-3,13-diaza-tricyclo[13.3.0.0*4,6*]-octadec-7-ene-4-carboxylic acid ethyl esterYield 75%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
95 °C

Procedure

The diene (1d) (1.75 g) was dissolved in dry dichloroethane (800 ml, 0.0046M solution). The solution was bubbled with argon for 10 min whereafter Hoveyda-Grubbs 1:st gen. catalyst (20 mg 3.5 mol %) was added and the reaction mixture was stirred at 95° C. overnight. Additional catalyst (25 mg) was added to the reaction mixture (at argon flow) and the reaction was stirred at 97° C. The reaction mixture was cooled to room temperature and scavenger (100 mg) was added and reaction mixture was stirred for 4 h at room temperature. The reaction mixture was filtered, the filtrate was concentrated by rotary evaporation and the residue was purified by column chromatography on silica which gave the pure title compound (1.23 g. Yield 75%).

Workup

  1. customThe solution was bubbled with argon for 10 min whereafter Hoveyda-Grubbs 1
  2. additioncatalyst (20 mg 3.5 mol %) was added
  3. additionAdditional catalyst (25 mg) was added to the reaction mixture (at argon flow)
  4. stirringthe reaction was stirred at 97° C
  5. temperatureThe reaction mixture was cooled to room temperature
  6. additionscavenger (100 mg) was added
  7. customreaction mixture
  8. stirringwas stirred for 4 h at room temperature
  9. filtrationThe reaction mixture was filtered
  10. concentrationthe filtrate was concentrated by rotary evaporation
  11. customthe residue was purified by column chromatography on silica which

Sources & evidence

ORD record
ord-6beee6afbefa4a34a498c53433804e2a
Source dataset
uspto-grants-2013_02
Patent number
US08383584B2

Reaction notes

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