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

HRID 1085527Notes

Reaction equation

HRID 1085527 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][CH2:16]1>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][CH2:16]1)=[O:11]

Participants

5

Reactant 2

HCID 27581482-(2,6-Dichlorophenyl)acetyl chlorideHCID 542272605'-Amino-2',3',5'-trideoxy-5-ethyluridine

Product 1

HCID 186333792',3',5'-Trideoxy-5'-[2(2,6-dichlorophenyl)acetamido]-5-ethyluridine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of (2,6-dichlorophenyl)acetyl chloride (prepared from 146 mg of the acid) in 1 ml of diethyl ether was added to a solution of 170 mg of 5'-amino-2',3',5'-trideoxy-5-ethyluridine in 2.72 ml of 0.26M sodium hydroxide solution and the mixture was shaken for 10 minutes. The mixture was filtered and the solid was recrystallized from 20 ml of ethanol to give 150 mg of 2',3',5'-trideoxy-5'-[2(2,6-dichlorophenyl)acetamido]-5-ethyluridine in the form of a white solid of melting point 237°-238° C.

Workup

  1. filtrationThe mixture was filtered
  2. customthe solid was recrystallized from 20 ml of ethanol

Sources & evidence

ORD record
ord-e92813be07a44c4d975db099de697a0d
Source dataset
uspto-grants-1991_04
Patent number
US05010060

Reaction notes

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