Cyclohexene → 4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-3-methyl-L-phenylalanine methyl ester

HRID 844881Notes

Reaction equation

HRID 844881 reaction equation
[CH3:1][O:2][C:3](=[O:35])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:24](=[O:33])[N:25]([CH3:32])[C:26](=[O:31])[N:27]([CH3:30])[C:28]=2[CH3:29])=[C:19]([CH3:34])[CH:18]=1)[NH:5]C(OCC1C=CC=CC=1)=O.C1CCCCC=1>[Pd].C(O)C>[CH3:1][O:2][C:3](=[O:35])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:24](=[O:33])[N:25]([CH3:32])[C:26](=[O:31])[N:27]([CH3:30])[C:28]=2[CH3:29])=[C:19]([CH3:34])[CH:18]=1)[NH2:5]

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 69335921N-(benzyloxycarbonyl)-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-3-methyl-L-phenylalanine methyl ester

Product 1

HCID 693365974-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-3-methyl-L-phenylalanine methyl esterYield 72%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of N-(benzyloxycarbonyl)-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-3-methyl-L-phenylalanine methyl ester (0.145 mmol, 70 mg), cyclohexene (1 mL) and 10% palladium on carbon (100 mg) in ethanol (2 mL) was heated to reflux for 15 h. Then, it was filtered through a pad of celite and the pad was washed with ethanol (10 mL). The combined filtrate was concentrated under reduced pressure. The residue was dried under high vacuum to afford 36 mg (72% yield) of 4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-3-methyl-L-phenylalanine methyl ester as a light yellow solid. ES-HRMS m/e calcd for C18H23N3O4 (M+Na) 368.1327, found 368.1321.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 15 h
  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 under reduced pressure
  6. customThe residue was dried under high vacuum

Sources & evidence

ORD record
ord-81f4000d2f184bf4b93057993e662db1
Source dataset
uspto-grants-2002_04
Patent number
US06380387B1

Reaction notes

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