2-(2,6-Dichlorophenyl)acetyl chloride → 5'-[2-(2,6-dichlorophenyl)-acetamido]-2',5'-dideoxy-3'-O-ethyl-5-ethyluridine

HRID 232351

Reaction equation

HRID 232351 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[O:30][CH2:31][CH3:32]>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[O:30][CH2:31][CH3:32])=[O:11]

Participants

5

Reactant 2

HCID 27581482-(2,6-Dichlorophenyl)acetyl chlorideHCID 186334585'-amino-2',5'-dideoxy-3'-O-ethyl-5-ethyluridine

Product 1

HCID 186334035'-[2-(2,6-dichlorophenyl)-acetamido]-2',5'-dideoxy-3'-O-ethyl-5-ethyluridine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of (2,6-dichlorophenyl)acetyl chloride (prepared from 103 mg of the acid) in 2 ml of diethyl ether was added to a solution of 140 mg of 5'-amino-2',5'-dideoxy-3'-O-ethyl-5-ethyluridine in 2.5 ml of 0.2M sodium hydroxide solution, the mixture was shaken vigorously for 10 minutes and then filtered. The solid was washed with 5 ml of water and 50 ml of diethyl ether, and then recrystallized from acetone to give 60 mg of 5'-[2-(2,6-dichlorophenyl)acetamido]-2',5'-dideoxy-3'-O-ethyl-5-ethyluridine in the form of a white solid of melting point 249°-250° C.

Workup

  1. filtrationfiltered
  2. washThe solid was washed with 5 ml of water and 50 ml of diethyl ether
  3. customrecrystallized from acetone

Sources & evidence

ORD record
ord-4307c2e0c7fd46529a23e4055a02ddb2
Source dataset
uspto-grants-1989_07
Patent number
US04851519

Linked notes

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