1-({4-(tert-Butyl-dimethyl-silanyloxy)-1-[hept-6-enyl-(4-methoxy-benzyl)-carbamoyl]-pyrrolidine-2-carbonyl}-amino)-2-vinyl-cyclopropanecarboxylic acid ethyl ester → 18-(tert-Butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyl)-2,15-dioxo-3,14,16-triaza-tricyclo[14.3.0.0*4,6*]nonadec-7-ene-4-carboxylic acid ethyl ester

HRID 1445423Notes

Reaction equation

HRID 1445423 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[CH2:18][CH:17]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH2:16][N:15]2[C:27](=[O:45])[N:28]([CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]C=C)[CH2:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)=[O:13])[CH2:8][CH:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2]>ClCCCl.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:10][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][N:28]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=1)[C:27](=[O:45])[N:15]1[CH:14]([CH2:18][CH:17]([O:19][Si:20]([C:23]([CH3:25])([CH3:24])[CH3:26])([CH3:22])[CH3:21])[CH2:16]1)[C:12](=[O:13])[NH:11]2)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 686758741-({4-(tert-Butyl-dimethyl-silanyloxy)-1-[hept-6-enyl-(4-methoxy-benzyl)-carbamoyl]-pyrrolidine-2-carbonyl}-amino)-2-vinyl-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 6687134618-(tert-Butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyl)-2,15-dioxo-3,14,16-triaza-tricyclo[14.3.0.0*4,6*]nonadec-7-ene-4-carboxylic acid ethyl esterYield 48%

Reagents, catalysts & solvents 2

HCID 11763533(1,3-Bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene)(dichloro)((2-((propan-2-yl)oxy)phenyl)methylidene)rutheniumCatalystHCID 111,2-DichloroethaneSolvent

Procedure

The diene (125) (1 g, 1.6 mmol) was dissolved in degassed DCE (1000 ml), Hoveyda-Grubbs 2nd generation (100 mg, 0.16 mmol) was added and the reaction mixture was refluxed under an atmosphere of argon overnight. The reaction mixture was evaporated on silica and purified by column chromatography on silica gel (30% EtOAc in Heptane→50% EtOAc in Heptane) to give the title compound (470 mg, 0.767 mmol, 48%). M+H=614.

Workup

  1. temperaturethe reaction mixture was refluxed under an atmosphere of argon overnight
  2. customThe reaction mixture was evaporated on silica
  3. custompurified by column chromatography on silica gel (30% EtOAc in Heptane→50% EtOAc in Heptane)

Sources & evidence

ORD record
ord-8fc42407e7c74690a845e0e973c3ce8f
Source dataset
uspto-grants-2010_02
Patent number
US07666834B2

Reaction notes

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