HCID 86655969, compound → Benzyl((8S,11R)-8-isopropyl-10-oxo-6-oxa-1,9,14-triazabicyclo[11.2.1]hexadeca-3,13(16),14-trien-11-yl)carbamate

HRID 2040011Notes

Reaction equation

HRID 2040011 reaction equation
[CH2:1]([N:4]1[CH:8]=[C:7]([CH2:9][C@@H:10]([NH:23][C:24](=[O:33])[O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:11](=[O:22])[NH:12][C@H:13]([CH2:17][O:18][CH2:19][CH:20]=[CH2:21])[CH:14]([CH3:16])[CH3:15])[N:6]=[CH:5]1)C=C>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>[CH:14]([C@@H:13]1[NH:12][C:11](=[O:22])[C@H:10]([NH:23][C:24](=[O:33])[O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:9][C:7]2=[CH:8][N:4]([CH:5]=[N:6]2)[CH2:1][CH:21]=[CH:20][CH2:19][O:18][CH2:17]1)([CH3:15])[CH3:16]

Participants

5

Reactant 1

HCID 86655969HCID 86655969, compound

Product 1

HCID 86655968Benzyl((8S,11R)-8-isopropyl-10-oxo-6-oxa-1,9,14-triazabicyclo[11.2.1]hexadeca-3,13(16),14-trien-11-yl)carbamateYield 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-e9ad1e589eb84936bb6a05cd74ddf6bb
Source dataset
uspto-grants-2013_11
Patent number
US08580777B2

Reaction notes

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