Dicyclohexylcarbodiimide → N-lysyl-5'-O-palmitoyl-deoxycytidine

HRID 378823Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 378823
[C:1]([O:18][CH2:19][C@H:20]1[O:24][C@@H:23]([N:25]2[CH:32]=[CH:31][C:29]([NH2:30])=[N:28][C:26]2=[O:27])[CH2:22][C@@H:21]1[OH:33])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C(OC([N:41](C(OC(C)(C)C)=O)[C@H:42]([C:48](O)=[O:49])[CH2:43][CH2:44][CH2:45][CH2:46][NH2:47])=O)(C)(C)C.C1(N=C=NC2CCCCC2)CCCCC1>CC(N(C)C)=O>[NH2:41][C@H:42]([C:48]([NH:30][C:29]1[CH:31]=[CH:32][N:25]([C@@H:23]2[O:24][C@H:20]([CH2:19][O:18][C:1](=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C@@H:21]([OH:33])[CH2:22]2)[C:26](=[O:27])[N:28]=1)=[O:49])[CH2:43][CH2:44][CH2:45][CH2:46][NH2:47]

Komponenten

5

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 154843895'-O-palmitoyldeoxycytidineHCID 22792075Di-tert-butoxycarbonyl-lysine

Produkt 1

HCID 15484390N-lysyl-5'-O-palmitoyl-deoxycytidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
4 °C

Versuchsvorschrift

14 grams of 5′-O-palmitoyl-deoxycytidine is dissolved in 100 ml dimethylacetamide, 1 molar equivalent of di-tert-butoxycarbonyl-lysine is added, and the mixture is cooled in an ice bath. 1.2 molar equivalents (7.4 g) of dicyclohexylcarbodiimide are added and the mixture is stirred at 4° C. for 90 hours. The precipitate (dicyclohexylurea) is removed by filtration. 100 ml of water is added to the filtrate, followed by 1 liter of ethyl acetate.

Aufarbeitung

  1. temperaturethe mixture is cooled in an ice bath
  2. customThe precipitate (dicyclohexylurea) is removed by filtration
  3. addition100 ml of water is added to the filtrate

Quellen und Nachweise

ORD-Eintrag
ord-207a4705b1e24a71808aaae7ffaa6e3f
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06297222B1

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