HCID 14997842, compound → HCID 14997851, compound

HRID 728619Notes

Reaction equation

HRID 728619 reaction equation
C(OC([O:11][CH2:12][C@H:13]1[O:17][C@@H:16]([N:18]2[CH:25]=[C:24]([F:26])[C:22](=[O:23])[NH:21][C:19]2=[O:20])[C@H:15]([O:27][C:28](=[O:40])[CH2:29][NH:30][C:31](=[O:39])[CH:32]([CH2:36][CH2:37][CH3:38])[CH2:33][CH2:34][CH3:35])[C@@H:14]1[O:41][C:42](=[O:54])[CH2:43][NH:44][C:45](=[O:53])[CH:46]([CH2:50][CH2:51][CH3:52])[CH2:47][CH2:48][CH3:49])=O)C1C=CC=CC=1>C(O)C.[C].[Pd]>[CH2:33]([CH:32]([CH2:36][CH2:37][CH3:38])[C:31]([NH:30][CH2:29][C:28]([O:27][C@@H:15]1[C@H:14]([O:41][C:42](=[O:54])[CH2:43][NH:44][C:45](=[O:53])[CH:46]([CH2:50][CH2:51][CH3:52])[CH2:47][CH2:48][CH3:49])[C@@H:13]([CH2:12][OH:11])[O:17][C@H:16]1[N:18]1[CH:25]=[C:24]([F:26])[C:22](=[O:23])[NH:21][C:19]1=[O:20])=[O:40])=[O:39])[CH2:34][CH3:35]

Participants

4

Reactant 1

HCID 14997842HCID 14997842, compound

Product 1

HCID 14997851HCID 14997851, compoundYield 70.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

After dissolving 0.62 g of 5'-O-benzyloxycarbonyl-2',3'-bis-O-[N-(2-n-propyl-n-pentanoyl)glycyl]-5-fluorouridine in 25 ml of ethanol, 0.2 g of 5% palladium carbon was added to the solution and the mixture was stirred under hydrogen stream, at room temperature and atmospheric pressure for 50 minutes. After the catalyst was filtered off, the residue obtained by condensing the reaction mixture under reduced pressure was applied to silica gel column chromatography to give 0.36 g (Yield: 68%) of the title compound.

Workup

  1. additionwas added to the solution
  2. filtrationAfter the catalyst was filtered off
  3. customthe residue obtained by condensing the reaction mixture under reduced pressure

Sources & evidence

ORD record
ord-a735f100b22943ed91a7ce141121a064
Source dataset
uspto-grants-1991_09
Patent number
US05049551

Reaction notes

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