Cyclohexene → N-[3-carboxy-2-(2-methylpropyl)propenoyl]-O-methyl-L-tyrosine N-methylamide

HRID 1252386Notes

Reaction equation

HRID 1252386 reaction equation
[CH3:1][NH:2][C:3](=[O:33])[C@H:4]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)[NH:5][C:6](=[O:23])[C:7]([CH2:19][CH:20]([CH3:22])[CH3:21])=[CH:8][C:9]([O:11]CC1C=CC=CC=1)=[O:10].C1CCCCC=1>C(O)C.[Pd]>[CH3:1][NH:2][C:3](=[O:33])[C@H:4]([CH2:24][C:25]1[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=1)[NH:5][C:6](=[O:23])[C:7]([CH2:19][CH:20]([CH3:21])[CH3:22])=[CH:8][C:9]([OH:11])=[O:10]

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 54339944HCID 54339944, compound

Product 1

HCID 53921771N-[3-carboxy-2-(2-methylpropyl)propenoyl]-O-methyl-L-tyrosine N-methylamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

E and Z N-[3-(benzyloxycarbonyl)-2-(2-methylpropyl)propenoyl]-O-methyl-L-tyrosine N-methylamide (3.0 g.) was heated under reflux for 2 hours in ethanol (60 mls.) and cyclohexene (30 mls.) in the presence of 10% palladium on charcoal (0.75 g.). The resultant reaction mixture was filtered through Celite and the solvent removed by evaporation in vacuo to yield a gum. This gum was crystallized from methanol/water to yield E and Z N-[3-carboxy-2-(2-methylpropyl)propenoyl]-O-methyl-L-tyrosine N-methylamide.

Workup

  1. customThe resultant reaction mixture
  2. filtrationwas filtered through Celite
  3. customthe solvent removed by evaporation in vacuo
  4. customto yield a gum
  5. customThis gum was crystallized from methanol/water

Sources & evidence

ORD record
ord-3bad0e6414994a1483abd5b80414f95f
Source dataset
uspto-grants-1988_05
Patent number
US04743587

Reaction notes

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