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

HRID 232349

Reaktionsgleichung

Reaktionsgleichung von HRID 232349
[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 solid of melting point 174°-177° C.

Aufarbeitung

  1. filtrationfiltered
  2. customThe solid was recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-234aa9b0397c47b49f76d83ad870af51
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04851519

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