Reacción #657302

ord-a0f28376eb6e484d8d3d0ea5f5944651

Ecuación de reacción

C=CCCCCCN(Cc1ccc(OC)cc1)C(=O)N1CC(OC(=O)c2ccc([N+](=O)[O-])cc2)CC1C(=O)NC1(C(=O)OCC)CC1C=C
Compound 25
C=CCCCCCN(Cc1ccc(OC)cc1)C(=O)N1CC(OC(=O)c2ccc([N+](=O)[O-])cc2)CC1C(=O)NC1(C(=O)OCC)CC1C=C
4-Nitro-benzoic acid 5-(1-ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-1-[hept-6-enyl-(4-methoxy-benzyl)-carbamoyl]-pyrrolidin-3-yl ester
→
CCOC(=O)C12CC1C=CCCCCCN(Cc1ccc(OC)cc1)C(=O)N1CC(OC(=O)c3ccc([N+](=O)[O-])cc3)CC1C(=O)N2
14-(4-Methoxy-benzyl)-18-(4-nitro-benzoyloxy)-2,15-dioxo-3,14,16-triaza-tricyclo[14.3.0.0*4,6*]nonadec-7-ene-4-carboxylic acid ethyl ester

Reactantes

C=CCCCCCN(Cc1ccc(OC)cc1)C(=O)N1CC(OC(=O)c2ccc([N+](=O)[O-])cc2)CC1C(=O)NC1(C(=O)OCC)CC1C=C
Compound 25
C=CCCCCCN(Cc1ccc(OC)cc1)C(=O)N1CC(OC(=O)c2ccc([N+](=O)[O-])cc2)CC1C(=O)NC1(C(=O)OCC)CC1C=C
4-Nitro-benzoic acid 5-(1-ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-1-[hept-6-enyl-(4-methoxy-benzyl)-carbamoyl]-pyrrolidin-3-yl ester

Reactivos

Cc1cc(C)c(N2CCN(c3c(C)cc(C)cc3C)[C]2=[Ru]([Cl])([Cl])=[CH]c2ccccc2OC(C)C)c(C)c1
Hoveyda-Grubbs Catalyst 2nd generation

Disolventes

ClCCCl
DCE

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otrodegassed
  2. 2
    Temperaturathe solution was heated to reflux
  3. 3
    OtroAfter 3 h the solution was evaporated

Procedimiento

Compound 25 (406 mg, 0.6 mmol) was dissolved in DCE (250 ml) and degassed. Hoveyda-Grubbs Catalyst 2nd generation (26 mg, 0.042 mmol) was added and the solution was heated to reflux. After 3 h the solution was evaporated and used direct in the next step.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09023808B2uspto-grants-2015_05