Benzoyl chloride → N-[5-(5-Ethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl]-benzamide

HRID 232344

Reaction equation

HRID 232344 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][CH2:11][C@H:12]1[O:16][C@@H:15]([N:17]2[CH:24]=[C:23]([CH2:25][CH3:26])[C:21](=[O:22])[NH:20][C:18]2=[O:19])[CH2:14][C@@H:13]1[OH:27]>[OH-].[Na+]>[C:1]([NH:10][CH2:11][C@H:12]1[O:16][C@@H:15]([N:17]2[CH:24]=[C:23]([CH2:25][CH3:26])[C:21](=[O:22])[NH:20][C:18]2=[O:19])[CH2:14][C@@H:13]1[OH:27])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 4518285'-Amino-2',5'-dideoxy-5-ethyluridine

Product 1

HCID 5275928N-[5-(5-Ethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl]-benzamideYield 39.1%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

140 mg of benzoyl chloride were added to a solution of 255 mg of 5'-amino-2',5'-dideoxy-5-ethyluridine in 3 ml of 0.33M sodium hydroxide solution and the mixture was shaken vigorously for 5 minutes. The mixture was filtered and the solid was washed with 5 ml of water and 5 ml of diethyl ether, and recrystallized from ethanol to give 140 mg of 5'-benzamido-2',5'-dideoxy-5-ethyluridine of melting point 246°-247° C.

Workup

  1. filtrationThe mixture was filtered
  2. washthe solid was washed with 5 ml of water and 5 ml of diethyl ether
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-bf30dc07242a451c8020cd6404ab2d12
Source dataset
uspto-grants-1989_07
Patent number
US04851519

Linked notes

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