HCID 68541620, compound → HCID 91026975, compound

HRID 1432092Notes

Reaction equation

HRID 1432092 reaction equation
[CH2:1]([S:7]([CH2:10][C@@H:11]([CH3:30])[C:12]([NH:14][C@H:15]([C@@H:23]1[CH2:27][C@@H:26]([CH3:28])[C:25](=[O:29])[O:24]1)[CH2:16][C@H:17]([CH3:22])[CH2:18][CH2:19]C=C)=[O:13])(=[O:9])=[O:8])[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6]>C(Cl)Cl.CC1C=C(C)C(N2C(=[Ru](Cl)(Cl)=CC3C=CC=CC=3)N(C3C(C)=CC(C)=CC=3C)CC2)=C(C)C=1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1>[CH3:30][C@H:11]1[C:12](=[O:13])[NH:14][C@H:15]([C@@H:23]2[CH2:27][C@@H:26]([CH3:28])[C:25](=[O:29])[O:24]2)[CH2:16][C@H:17]([CH3:22])[CH2:18][CH2:19][CH:6]=[CH:5][CH2:4][CH2:3][CH2:2][CH2:1][S:7](=[O:9])(=[O:8])[CH2:10]1

Participants

4

Reactant 1

HCID 68541620HCID 68541620, compound

Product 1

HCID 91026975HCID 91026975, compound

Reagents, catalysts & solvents 2

HCID 11147261(1,3-Dimesitylimidazolidin-2-ylidene)(tricyclohexylphosphine)benzylidene ruthenium dichlorideCatalystHCID 6344DichloromethaneSolvent3×

Procedure

Under a nitrogen atmosphere to 200 ml refluxing DCM is added a solution of 10 mg (0.01 mmol) tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidine]ruthenium(IV)dichloride (‘Grubbs 2’ catalyst) in 1 ml DCM, followed by the dropwise addition of a solution of 100 mg (0.218 mmol) (S)-3-(hex-5-ene-1-sulfonyl)-2-methyl-N-[(1S,3R)-3-methyl-1-((2S,4R)-4-methyl-5-oxo-tetrahydro-furan-2-yl)hept-6-enyl]-propionamide in 5 ml DCM. After 2 h the mixture is cooled to rt and quenched by the addition of 0.05 ml butyl vinyl ether and 0.2 g activated charcoal. The mixture is passed through a pad of silica gel (EtOAc/hexane 1:1) to yield the title compound as a solid.

Workup

  1. customquenched by the addition of 0.05 ml butyl vinyl ether and 0.2 g

Sources & evidence

ORD record
ord-d8e34d938f504e1f88ffa78e056d8e87
Source dataset
uspto-grants-2009_11
Patent number
US07612055B2

Reaction notes

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