HCID 86611579, compound → HCID 68542589, compound

HRID 1432080Notes

Reaction equation

HRID 1432080 reaction equation
[Cl:1][CH2:2][CH:3]([C@H:5]([NH:13][C:14]([C@@H:16]([N:18]([CH3:27])[C:19](=[O:26])[CH2:20][CH2:21][CH2:22][CH2:23][CH:24]=[CH2:25])[CH3:17])=[O:15])[CH2:6][CH:7]([CH3:12])[CH2:8][CH2:9]C=C)[OH:4]>C(Cl)Cl.Cl[Ru](=C1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)(Cl)(=CC1C=CC=CC=1)[P](C1CCCCC1)(C1CCCCC1)C1CCCCC1>[Cl:1][CH2:2][CH:3]([CH:5]1[NH:13][C:14](=[O:15])[C@H:16]([CH3:17])[N:18]([CH3:27])[C:19](=[O:26])[CH2:20][CH2:21][CH2:22][CH2:23][CH:24]=[CH:25][CH2:9][CH2:8][C@@H:7]([CH3:12])[CH2:6]1)[OH:4]

Participants

4

Reactant 1

HCID 86611579HCID 86611579, compound

Product 1

HCID 68542589HCID 68542589, compound

Reagents, catalysts & solvents 2

HCID 178425456HCID 178425456, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1.38 g (3.44 mmol) hept-6-enoic acid {(S)-1-[(R)-1-(2-chloro-1-hydroxy-ethyl)-3-methyl-hept-6-enylcarbamoyl]-ethyl}-methyl-amide in 17 ml DCM is added dropwise within an hour to a refluxing solution of 146 mg [1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene)-dichloro(phenylmethylene)-(tricyclohexylphosphine)ruthenium](Grubbs II catalyst) in 340 ml DCM. The mixture is refluxed for an additional hour and the solvent evaporated. The residue is purified by chromatography on silica gel (DCM/methanol 95/5), giving the desired product as a brownish foam (mixture of diastereomers).

Workup

  1. temperatureThe mixture is refluxed for an additional hour
  2. customthe solvent evaporated
  3. customThe residue is purified by chromatography on silica gel (DCM/methanol 95/5)

Sources & evidence

ORD record
ord-8c06e6315a57499880d02239268253a2
Source dataset
uspto-grants-2009_11
Patent number
US07612055B2

Reaction notes

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