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

HRID 1085519

Reaktionsgleichung

Reaktionsgleichung von HRID 1085519
[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][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(OCC)C.[OH-].[Na+]>[CH2:31]([O:30][C@@H:16]1[C@@H:15]([CH2:14][NH:13][C:10](=[O:11])[CH2:9][C:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=2[Cl:8])[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]1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Komponenten

5

Edukt 2

HCID 27581482-(2,6-Dichlorophenyl)acetyl chlorideHCID 186334595'-amino-3'-O-benzyl-2',5'-dideoxy-5-ethyluridine

Produkt 1

HCID 186333993'-O-benzyl-5'-[2-(2,6-dichlorophenyl)acetamido]2',5'-dideoxy-5-ethyluridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

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 173 mg of 5'-amino-3'-O-benzyl- 2',5'-dideoxy-5-ethyluridine in 4.5 ml of 0.11M sodium hydroxide solution. The mixture was shaken vigorously for 10 minutes and then filtered. The solid was recrystallized from ethanol to give 120 mg of 3'-O-benzyl-5'-[2-(2,6-dichlorophenyl)acetamido]2',5'-dideoxy-5-ethyluridine in the form of a white solis of melting point 174°-177° C.

Aufarbeitung

  1. filtrationfiltered
  2. customThe solid was recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-b4d092d6d4fe4a4a85df203125ed5f5a
Quelldatensatz
uspto-grants-1991_04
Patentnummer
US05010060

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