HCID 68592522, compound → HCID 68589639, compound

HRID 1429148Notes

Reaction equation

HRID 1429148 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]([O:26][CH3:27])[N:23]=[C:22]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[N:21]=3)[CH2:16][CH:15]2[C:34](=[O:43])[N:35]([CH2:37][CH2:38][CH2:39][CH2:40][CH:41]=[CH2:42])[CH3:36])=[O:13])[CH2:8][CH:7]1C=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:42]=[CH:41][CH2:40][CH2:39][CH2:38][CH2:37][N:35]([CH3:36])[C:34](=[O:43])[CH:15]1[CH:14]([CH2:18][CH:17]([O:19][C:20]3[CH:25]=[C:24]([O:26][CH3:27])[N:23]=[C:22]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[N:21]=3)[CH2:16]1)[C:12](=[O:13])[NH:11]2)=[O:5])[CH3:2]

Participants

3

Reactant 1

HCID 68592522HCID 68592522, compound

Product 1

HCID 68589639HCID 68589639, compoundYield 38.1%

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 7c (1 g, 1.69 mmol) and Hoveyda-Grubbs catalyst, 2nd generation (100 mg) were dissolved in degassed and dry DCE (1000 ml). The mixture was heated to reflux temperature over night under N2-atmosphere. The material was mixed with silica and the solvent was evaporated. Purification by column chromatography, EtOAc/Heptane 30:70→50:50 gave the title compound (362 mg, 38%), MS (M+H)+563.

Workup

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

Sources & evidence

ORD record
ord-e43c10bf93b743a5bd85fe6f306b167e
Source dataset
uspto-grants-2015_01
Patent number
US08937080B2

Reaction notes

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