1,4-Cyclohexadiene → HCID 10949694, compound

HRID 2249154Notes

Reaction equation

HRID 2249154 reaction equation
C(OC([NH:11][C@H:12]([C:16]([O:18][CH2:19][CH:20]([O:40][CH2:41][N:42]1[CH:47]=[CH:46][C:45]([NH2:48])=[N:44][C:43]1=[O:49])[CH2:21][O:22][C:23](=[O:39])[C@H:24]([CH:36]([CH3:38])[CH3:37])[NH:25]C(OCC1C=CC=CC=1)=O)=[O:17])[CH:13]([CH3:15])[CH3:14])=O)C1C=CC=CC=1.C1CC=CCC=1>[Pd].C(O)(=O)C>[NH2:25][C@H:24]([C:23]([O:22][CH2:21][CH:20]([O:40][CH2:41][N:42]1[CH:47]=[CH:46][C:45]([NH2:48])=[N:44][C:43]1=[O:49])[CH2:19][O:18][C:16](=[O:17])[C@H:12]([CH:13]([CH3:15])[CH3:14])[NH2:11])=[O:39])[CH:36]([CH3:38])[CH3:37]

Participants

5

Reactant 2

HCID 123431,4-CyclohexadieneHCID 67792235HCID 67792235, compound

Product 1

HCID 10949694HCID 10949694, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent2×

Procedure

To a cool mixture of 3.44 g of 2-((4-amino-1,2-dihydro-2-oxo-1-pyrimidinyl)methoxy)-1,3-propanediyl bis(N-((benzyloxy)carbonyl)-L-valinate) and 7 g of 10% palladium catalyst in acetic acid was slowly added 8.65 mL of 1,4-cyclohexadiene. The mixture was allowed to stir at room temperature for 18 h. The reaction mixture was filtered through a pad of Celite. The filtrate was then concentrated and dried in the lyophilizer for 48 h. The resulting beige foam was scraped off affording 2.38 g (68%, as the acetic acid salt) of the title compound. The elemental analysis (showing 2M of acetic acid and 1M of water) UV, 1H, 13C-NMR spectra were consistent with the title structure.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. concentrationThe filtrate was then concentrated
  3. customdried in the lyophilizer for 48 h
  4. customaffording 2.38 g (68%

Sources & evidence

ORD record
ord-7533940437484142bf1dc72873e2febd
Source dataset
uspto-grants-1991_08
Patent number
US05043339

Reaction notes

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