HCID 86655969, compound → HCID 86655968, compound

HRID 626638

Reaction equation

HRID 626638 reaction equation
[CH2:1]([O:8][C:9](=[O:33])[NH:10][C@@H:11]([C:21](=[O:32])[NH:22][C@H:23]([CH2:27][O:28][CH2:29][CH:30]=C)[CH:24]([CH3:26])[CH3:25])[CH2:12][C:13]1[N:14]=[CH:15][N:16]([CH2:18][CH:19]=C)[CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>ClCCl.Cl[Ru](=C1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)(Cl)(=CC1C=CC=CC=1)[P](C1CCCCC1)(C1CCCCC1)C1CCCCC1>[CH2:1]([O:8][C:9](=[O:33])[NH:10][C@@H:11]1[CH2:12][C:13]2=[CH:17][N:16]([CH:15]=[N:14]2)[CH2:18][CH:19]=[CH:30][CH2:29][O:28][CH2:27][C@H:23]([CH:24]([CH3:25])[CH3:26])[NH:22][C:21]1=[O:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 86655969HCID 86655969, compound

Product 1

HCID 86655968HCID 86655968, compoundYield 73.2%

Reagents, catalysts & solvents 3

HCID 11147261(1,3-Dimesitylimidazolidin-2-ylidene)(tricyclohexylphosphine)benzylidene ruthenium dichlorideCatalystHCID 178425456HCID 178425456, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 0.735 g (1.62 mmol) of benzyl[(R)-2-(1-allyl-1H-imidazol-4-yl)-1-((S)-1-allyloxymethyl-2-methylpropylcarbamoyl)ethyl]carbamate in 370 ml of dichloromethane was mixed with 0.210 g (0.24 mmol) of benzylidene[1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(tricyclohexylphosphine)ruthenium (Grubbs II catalyst) and stirred at RT. The mixture was stirred at RT for several days with repeated addition of Grubbs II catalyst until starting material was no longer present (LC/MS). The mixture was concentrated and the residue was chromatographed on silica gel (dichloromethane/methanol 99:1→9:1). 0.506 g of the title compound was obtained.

Workup

  1. stirringThe mixture was stirred at RT for several days
  2. concentrationThe mixture was concentrated
  3. customthe residue was chromatographed on silica gel (dichloromethane/methanol 99:1→9:1)

Sources & evidence

ORD record
ord-bb6be0ca53ed4ae6891a7462896bf134
Source dataset
uspto-grants-2016_04
Patent number
US09309207B2

Linked notes

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