Water → HCID 86745015, compound

HRID 2249153Notes

Reaction equation

HRID 2249153 reaction equation
C(OC([NH:11][C@H:12]([C:17]([O:19][CH2:20][CH:21]([O:42][CH2:43][N:44]1[CH:49]=[CH:48][C:47]([NH2:50])=[N:46][C:45]1=[O:51])[CH2:22][O:23][C:24](=[O:41])[C@H:25]([C@H:37]([CH2:39][CH3:40])[CH3:38])[NH:26]C(OCC1C=CC=CC=1)=O)=[O:18])[C@H:13]([CH2:15][CH3:16])[CH3:14])=O)C1C=CC=CC=1.C1CC=CCC=1.O>[Pd].C(O)(=O)C>[NH2:11][C@H:12]([C:17]([O:19][CH2:20][CH:21]([O:42][CH2:43][N:44]1[CH:49]=[CH:48][C:47]([NH2:50])=[N:46][C:45]1=[O:51])[CH2:22][O:23][C:24](=[O:41])[C@H:25]([C@H:37]([CH2:39][CH3:40])[CH3:38])[NH2:26])=[O:18])[C@H:13]([CH2:15][CH3:16])[CH3:14]

Participants

6

Reactant 3

HCID 962WaterHCID 123431,4-CyclohexadieneHCID 67821021HCID 67821021, compound

Product 1

HCID 86745015HCID 86745015, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent3×

Procedure

To a cool mixture of 2.54 g of 2-((4-amino-1,2-dihydro-2-oxo-1-pyrimidinyl)methoxy)-1,3-propanediyl bis(N-((benzyloxy)carbonyl)-L-isoleucinate) and 5.16 g of 10% palladium catalyst in acetic acid was slowly added 6.4 mL of 1,4-cyclohexadiene. The mixture was allowed to stir at room temperature for 3 h. The reaction mixture was filtered through a pad of Celite, the filtrate was then concentrated and dried in the lyophiliser for 3 d. The residue was scraped off, affording 2.079 g (82%, as the acetic acid salt) of a beige foam. 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 lyophiliser for 3 d
  4. customaffording 2.079 g (82%

Sources & evidence

ORD record
ord-15fcf61b9a554a68928de5c6fa22810d
Source dataset
uspto-grants-1991_08
Patent number
US05043339

Reaction notes

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