HCID 18633382, compound → HCID 53989383, compound

HRID 232362Notes

Reaction equation

HRID 232362 reaction equation
[CH2:1]([C:3]1[C:4](=[O:30])[NH:5][C:6](=[O:29])[N:7]([CH:28]=1)[C@@H:8]1[O:27][C@H:12]([CH2:13][NH:14][C:15](=[O:26])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N+:23]([O-])=O)[C@@H:10]([OH:11])[CH2:9]1)[CH3:2].[H][H]>C(O)C.[Pd]>[NH2:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH2:16][C:15]([NH:14][CH2:13][C@H:12]1[O:27][C@@H:8]([N:7]2[CH:28]=[C:3]([CH2:1][CH3:2])[C:4](=[O:30])[NH:5][C:6]2=[O:29])[CH2:9][C@@H:10]1[OH:11])=[O:26]

Participants

5

Reactant 2

HCID 18633382HCID 18633382, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53989383HCID 53989383, compoundYield 53.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 0.2 g of 2',5'-dideoxy-5-ethyl-5'-[2-(2-nitrophenyl)acetamido]uridine in 100 ml of ethanol was hydrogenated over 0.1 g of 10% palladium-on-carbon catalyst at room temperature and under atmospheric pressure until the uptake of hydrogen was complete. The mixture was filtered and the filtrate was evaporated to yield an oil which crystallized from ethanol to give 0.1 g of 5'-[2-(2-aminophenyl)acetamido]-2',5'-dideoxy-5-ethyluridine in the form of a white solid of melting point 195°-196° C.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated
  3. customto yield an oil which
  4. customcrystallized from ethanol

Sources & evidence

ORD record
ord-a43c8734b9bc409dae948dae5911886c
Source dataset
uspto-grants-1989_07
Patent number
US04851519

Reaction notes

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