Cyclohexene → Phenylalanine anilide

HRID 1289071Notes

Reaction equation

HRID 1289071 reaction equation
[C:1]1([NH:7][C:8](=[O:28])[C@H:9]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[NH:10]C(OCC2C=CC=CC=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1CCCCC=1>C(O)C.[Pd]>[C:1]1([NH:7][C:8](=[O:28])[C@H:9]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[NH2:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 7033973HCID 7033973, compound

Product 1

HCID 151952Phenylalanine anilide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Nα -Benzyloxycarbonyl-L-phenylalanine-N-phenylamide (2.50 g, 6.68 mmol) was dissolved in ethanol (20 ml) and cyclohexene (5 ml) and 10% palladium on charcoal (250 mg) was added. The mixture was heated at reflux for 1 hour after which time no starting material was detectable (as indicated by TLC analysis). The catalyst was removed by filtration and the solvent evaporated to leave the title compound contaminated with residual ethanol (1.74 g). 1H-NMR; d (CD3OD), 7.45 (2H, m), 7.18 (7H, m), 7.04 (1H, m), 3.56 (1H, m), 3.04 (1H, dd, J=6.4, 13.3 Hz) and 2.85 (1H, dd, J=7.2, 13.3 Hz).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 hour after which time no starting material
  3. customThe catalyst was removed by filtration
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-dc7f83b1de61493cb738eecf517fefad
Source dataset
uspto-grants-1998_05
Patent number
US05747514

Reaction notes

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