HCID 70399831, compound → HCID 18635810, compound

HRID 1638976Notes

Reaction equation

HRID 1638976 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:9](/[CH:10]=[CH:11]/[C:12](=[O:22])[CH2:13][C:14]2[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:21])[O:8][C@@H:7]([N:23]2[CH:30]=[C:29]([CH2:31][CH3:32])[C:27](=[O:28])[NH:26][C:24]2=[O:25])[CH2:6]1)(=[O:3])[CH3:2]>CO.[Pd]>[C:1]([O:4][C@@H:5]1[C@@H:9]([CH2:10][CH2:11][C:12](=[O:22])[CH2:13][C:14]2[C:15]([Cl:21])=[CH:16][CH:17]=[CH:18][C:19]=2[Cl:20])[O:8][C@@H:7]([N:23]2[CH:30]=[C:29]([CH2:31][CH3:32])[C:27](=[O:28])[NH:26][C:24]2=[O:25])[CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 70399831HCID 70399831, compound

Product 1

HCID 18635810HCID 18635810, compoundYield 73.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3.30 g of (E)-3'-O-acetyl-5'-[3-(2,6-dichlorophenyl)-2-oxopropylidene]-2',5'-dideoxy-5-ethyluridine in 1.50 l of methanol was hydrogenated over 1.10 g of 10% Pd/C catalyst at room temperature and under atmospheric pressure for 3 hours. The mixture was filtered and the filtrate was evaporated. The residue was triturated with diethyl ether to give 2.45 g of 3'-O-acetyl-5'-[3-(2,6-dichlorophenyl)-2-oxopropyl]-2',5'-dideoxy-5-ethyluridine, mp 186°.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated
  3. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-9cfbef3984294f0aa9a8ffd62b0f7ea1
Source dataset
uspto-grants-1989_11
Patent number
US04882316

Reaction notes

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