HCID 14849635, compound → HCID 14849651, compound

HRID 981729Notes

Reaction equation

HRID 981729 reaction equation
C([O:8][C:9]1[CH:52]=[CH:51][C:12]([CH2:13][C@@H:14]([C:26]([O:28][CH2:29][C@H:30]2[O:34][C@@H:33]([N:35]3[CH:42]=[C:41]([F:43])[C:39](=[O:40])[NH:38][C:36]3=[O:37])[CH2:32][C@@H:31]2[O:44][CH2:45][C:46]2[O:50][CH:49]=[CH:48][CH:47]=2)=[O:27])[NH:15]C(OCC2C=CC=CC=2)=O)=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>CO.[C].[Pd]>[F:43][C:41]1[C:39](=[O:40])[NH:38][C:36](=[O:37])[N:35]([CH:42]=1)[C@@H:33]1[O:34][C@H:30]([CH2:29][O:28][C:26](=[O:27])[C@H:14]([CH2:13][C:12]2[CH:51]=[CH:52][C:9]([OH:8])=[CH:10][CH:11]=2)[NH2:15])[C@@H:31]([O:44][CH2:45][C:46]2[O:50][CH:49]=[CH:48][CH:47]=2)[CH2:32]1

Participants

5

Reactant 2

HCID 14849635HCID 14849635, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14849651HCID 14849651, compoundYield 17.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1.10 g of 5'-O-(O-benzyl-N- benzyloxycarbonyl-L-tyrosyl)-2'-deoxy-5-fluoro-3'-O-furfuryluridine prepared in Example 14 in 50 ml of methanol was added 0.11 g of 5% palladium-carbon, and the mixture was stirred in a hydrogen stream under ambient temperature and pressure condition for 2 hours. The catalyst was filtered off, and the solvent was evaporated off under reduced pressure. The residue was placed on silica gel column and eluted with 5% methanol-chloroform for purification, thereby giving 0.13 g of 2'-deoxy-5- fluoro-3'-O-furfuryl-5'-O-L-tyrosyluridine.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was evaporated off under reduced pressure
  3. washeluted with 5% methanol-chloroform for purification

Sources & evidence

ORD record
ord-38eefd2bdcf54359a3f2aeb52ba1e321
Source dataset
uspto-grants-1991_02
Patent number
US04992534

Reaction notes

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