HCID 68590569, compound → HCID 68589805, compound

HRID 1429135Notes

Reaction equation

HRID 1429135 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[CH2:18][CH:17]([O:19][C:20]3[CH:25]=[C:24]([C:26]([CH3:29])([CH3:28])[CH3:27])[N:23]=[C:22]([O:30][CH3:31])[N:21]=3)[CH2:16][CH:15]2[C:32](=[O:41])[N:33]([CH2:35][CH2:36][CH2:37][CH2:38][CH:39]=C)[CH3:34])=[O:13])[CH2:8][CH:7]1[CH:9]=C)=[O:5])[CH3:2]>CC1C=C(C)C(N2C(=[Ru](Cl)(Cl)=CC3C=CC=CC=3OC(C)C)N(C3C(C)=CC(C)=CC=3C)CC2)=C(C)C=1>[CH2:1]([O:3][C:4]([C:6]12[CH2:8][CH:7]1[CH:9]=[CH:39][CH2:38][CH2:37][CH2:36][CH2:35][N:33]([CH3:34])[C:32](=[O:41])[CH:15]1[CH:14]([CH2:18][CH:17]([O:19][C:20]3[CH:25]=[C:24]([C:26]([CH3:28])([CH3:29])[CH3:27])[N:23]=[C:22]([O:30][CH3:31])[N:21]=3)[CH2:16]1)[C:12](=[O:13])[NH:11]2)=[O:5])[CH3:2]

Participants

3

Reactant 1

HCID 68590569HCID 68590569, compound

Product 1

HCID 68589805HCID 68589805, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 11763533(1,3-Bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene)(dichloro)((2-((propan-2-yl)oxy)phenyl)methylidene)rutheniumCatalyst

Procedure

Compound 3h (500 mg, 0.87 mmol) and Hoveyda-Grubbs catalyst, 2nd generation (50 mg) were dissolved in degassed and dry DCE (500 ml). The mixture was heated to reflux over night under N2-atmosphere. The material was mixed with silica, the solvent was evaporated and the residue was purified by column chromatography, EtOAc/Heptane 30:70→50:50 which gave the title compound (350 mg, 74%), MS (M+H)+543.

Workup

  1. customin degassed
  2. temperatureThe mixture was heated
  3. temperatureto reflux over night under N2-atmosphere
  4. additionThe material was mixed with silica
  5. customthe solvent was evaporated
  6. customthe residue was purified by column chromatography, EtOAc/Heptane 30:70→50:50 which

Sources & evidence

ORD record
ord-b0538ce6bc00418bb7b210203003b966
Source dataset
uspto-grants-2015_01
Patent number
US08937080B2

Reaction notes

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