5'-Amino-2',5'-dideoxy-5-ethyluridine → 2-(2,6-Dichloro-phenyl)-N-[(2R,3S,5R)-5-(5-ethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl]-acetamide

HRID 1085516Notes

Reaction equation

HRID 1085516 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][C:10](Cl)=[O:11].[NH2:13][CH2:14][C@H:15]1[O:19][C@@H:18]([N:20]2[CH:27]=[C:26]([CH2:28][CH3:29])[C:24](=[O:25])[NH:23][C:21]2=[O:22])[CH2:17][C@@H:16]1[OH:30]>C(OCC)C.[OH-].[Na+]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][C:10]([NH:13][CH2:14][C@H:15]1[O:19][C@@H:18]([N:20]2[CH:27]=[C:26]([CH2:28][CH3:29])[C:24](=[O:25])[NH:23][C:21]2=[O:22])[CH2:17][C@@H:16]1[OH:30])=[O:11]

Participants

5

Reactant 2

HCID 4518285'-Amino-2',5'-dideoxy-5-ethyluridineHCID 27581482-(2,6-Dichlorophenyl)acetyl chloride

Product 1

HCID 186334402-(2,6-Dichloro-phenyl)-N-[(2R,3S,5R)-5-(5-ethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl]-acetamideYield 69.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 1.12 g of (2,6-dichlorophenyl)acetyl chloride in 15 ml of diethyl ether was added to a solution of 1.275 g of 5'-amino-2',5'dideoxy-5-ethyluridine in 15 ml of 0.33M sodium hydroxide solution. The mixture was shaken vigorously for 10 minutes and then filtered. The solid was washed with 150 ml of water, 20 ml of ethanol and 40 ml of diethyl ether, and then recrystallized from 2.5 l of ethanol to give 1.53 g of 5'-[2-(2,6-dichlorophenyl)acetamido]-2', 5'-dideoxy-5-ethyluridine in the form of a white solid of melting point 296°-297° C.

Workup

  1. filtrationfiltered
  2. washThe solid was washed with 150 ml of water, 20 ml of ethanol and 40 ml of diethyl ether
  3. customrecrystallized from 2.5 l of ethanol

Sources & evidence

ORD record
ord-142991f5194444149e975fabf10715ee
Source dataset
uspto-grants-1991_04
Patent number
US05010060

Reaction notes

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