1,1'-Carbonyldiimidazole → HCID 5279008, Verbindung

HRID 1817516Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1817516
C([NH+](CC)CC)C.[N:8]([C@@H:11]1[C@@H:15]([CH2:16][P:17]([OH:20])(=[O:19])[OH:18])[O:14][C@@H:13]([N:21]2[CH:29]=[C:27]([CH3:28])[C:25](=[O:26])[NH:24][C:22]2=[O:23])[CH2:12]1)=[N+:9]=[N-:10].C(N1C=CN=C1)(N1C=CN=C1)=O.C([NH+](CCCC)CCCC)CCC.[O-:55][P:56]([NH:59][P:60]([O-])([O-:62])=[O:61])(=[O:58])[O-:57]>CN(P(N(C)C)(N(C)C)=O)C.O.CO>[CH3:28][C:27]1[C:25](=[O:26])[NH:24][C:22](=[O:23])[N:21]([C@@H:13]2[O:14][C@H:15]([CH2:16][P:17]([O:18][P:60]([OH:62])([NH:59][P:56]([OH:58])([OH:57])=[O:55])=[O:61])([OH:20])=[O:19])[C@@H:11]([N:8]=[N+:9]=[N-:10])[CH2:12]2)[CH:29]=1

Komponenten

9

Edukt 5

HCID 682631,1'-CarbonyldiimidazoleHCID 4725903'-Azido-3',5'-dideoxythymidine-5'-phosphonic acidHCID 1385867TriethylammoniumHCID 3724478TributylammoniumHCID 23278979Imidodiphosphate

Produkt 1

HCID 5279008HCID 5279008, VerbindungAusbeute 69,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 12679HexamethylphosphoramideLösungsmittel2×

Versuchsvorschrift

The triethylammonium salt of compound 53 (50.0 mg, 0.09 mmol) was dissolved in HMPA (2 mL) and 1,1′-carbonyldiimidazole (106 mg, 0.66 mmol) was added at room temperature and stirred for 2 h. Methanol (35 μL) was added and stirring was continued for 45 min. The tri-n-butylammonium salt of imidodiphosphate (427 mg, 0.46 mmol) dissolved in HMPA (2 mL) was added with syringe to the solution of activated AZT monophosphate, and the combined solution was stirred at room temperature for 4 h. The reaction mixture was cooled in ice-bath and water (5 mL) was added. Purification by HPLC gave 30.6 mg of the titled compound 57.

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for 45 min
  3. stirringthe combined solution was stirred at room temperature for 4 h
  4. temperatureThe reaction mixture was cooled in ice-bath
  5. customPurification by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-3b27cf3cd8294cb693cf898dda748d96
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07598230B2

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