Cyclohexene → HCID 69336446, compound

HRID 844875Notes

Reaction equation

HRID 844875 reaction equation
[CH3:1][O:2][C:3](=[O:34])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:24](=[O:32])[N:25]([CH3:31])[C:26](=[O:30])[N:27]([CH3:29])[CH:28]=2)=[C:19]([CH3:33])[CH:18]=1)[NH:5]C(OCC1C=CC=CC=1)=O.C1CCCCC=1>[Pd].C(O)C>[CH3:1][O:2][C:3](=[O:34])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:24](=[O:32])[N:25]([CH3:31])[C:26](=[O:30])[N:27]([CH3:29])[CH:28]=2)=[C:19]([CH3:33])[CH:18]=1)[NH2:5]

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 69336827HCID 69336827, compound

Product 1

HCID 69336446HCID 69336446, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of N-(benzyloxycarbonyl)-4-(1,3-dimethyl-2,4-dioxo-5-pyrimidinyl)-3-methyl-L-phenylalanine methyl ester (0.34 mmol, 159 mg), cyclohexene (1 mL) and 10% palladium on carbon (100 mg) in ethanol (3 mL) was heated to reflux for 20 min. Then, it was filtered through a pad of celite and the pad was washed with ethanol (10 mL). The combined filtrate was concentrated and the residue was dried under high vacuum to afford 96 mg (85% yield) of 4-(1,3-dimethyl-2,4-dioxo-5-pyrimidinyl)-3-methyl-L-phenylalanine methyl ester as a sticky yellow solid. ES-HRMS m/e calcd for C17H21N3O4 (M+Na) 354.1424, found 354.1424.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 20 min
  3. filtrationThen, it was filtered through a pad of celite
  4. washthe pad was washed with ethanol (10 mL)
  5. concentrationThe combined filtrate was concentrated
  6. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-96216ec1b71d4edc8c8bf47e0df197e0
Source dataset
uspto-grants-2002_04
Patent number
US06380387B1

Reaction notes

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