Water → N-Benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine

HRID 586766

Reaktionsgleichung

Reaktionsgleichung von HRID 586766
C(NC1C=CN([C@@H]2O[C@H](CO)[C@@H](O)C2)C(=O)N=1)(=O)C1C=CC=CC=1.C(NC1C=CN([C@@H]2O[C@H](CO)[C@@H](OC(C3C=CC=CC=3)(C3C=CC(OC)=CC=3)C3C=CC(OC)=CC=3)C2)C(=O)N=1)(=O)C1C=CC=CC=1.[C:72]([NH:80][C:81]1[CH:140]=[CH:139][N:84]([C@@H:85]2[O:115][C@H:89]([CH2:90][O:91][C:92]([C:109]3[CH:114]=[CH:113][CH:112]=[CH:111][CH:110]=3)([C:101]3[CH:106]=[CH:105][C:104]([O:107][CH3:108])=[CH:103][CH:102]=3)[C:93]3[CH:98]=[CH:97][C:96]([O:99][CH3:100])=[CH:95][CH:94]=3)[C@@:87](C(C3C=CC=CC=3)(C3C=CC(OC)=CC=3)C3C=CC(OC)=CC=3)([OH:88])[CH2:86]2)[C:83](=[O:141])[N:82]=1)(=[O:79])[C:73]1[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=1.O>C(#N)C>[C:72]([NH:80][C:81]1[CH:140]=[CH:139][N:84]([C@@H:85]2[O:115][C@H:89]([CH2:90][O:91][C:92]([C:109]3[CH:114]=[CH:113][CH:112]=[CH:111][CH:110]=3)([C:93]3[CH:98]=[CH:97][C:96]([O:99][CH3:100])=[CH:95][CH:94]=3)[C:101]3[CH:106]=[CH:105][C:104]([O:107][CH3:108])=[CH:103][CH:102]=3)[C@@H:87]([OH:88])[CH2:86]2)[C:83](=[O:141])[N:82]=1)(=[O:79])[C:73]1[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 9797617N4-Benzoyl-2'-deoxycytidineHCID 15403758N4-Benzoyl-3'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidineHCID 86590472N4-benzoyl-3',5'-O-bis(4,4'-dimethoxytrityl)-2'-deoxycytidine

Produkt 1

HCID 2724490N-Benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Referring to PCT Publication No. WO00/75154, the non-hydrated N4-benzoyl-5′-O-(4, 4′-dimethoxytrityl)-2′-deoxycytidine (2.00 g), including N4-benzoyl-2′-deoxycytidine, N4-benzoyl-3′-O-(4, 4′-dimethoxytrityl)-2′-deoxycytidine, and N4-benzoyl-3′, 5′-O-bis(4, 4′-dimethoxytrityl)-2′-deoxycytidine with rates by peak areas of 1.0%, 0.15%, and 2.2%, respectively, was dissolved in acetonitrile (2.3 mL). The solution was added dropwise to water (41 mL) with vigorous stirring and the resultant mixture was stirred for one hour. A white precipitate was recovered by filtration, was washed twice with water and was dried at 50° C. in a vacuum to yield N4-benzoyl-5′-O-(4, 4′-dimethoxytrityl)-2′-deoxycytidine (1.82 g). The XRD pattern and the DSC thermogram showed neither an absorption peak nor an endothermic peak due to the crystallization, which indicates the resultant components was not crystallized. Moreover, the component contained N4-benzoyl-2′-deoxycytidine, N4-benzoyl-3′-O-(4, 4′-dimethoxytrityl)-2′-deoxycytidine, and N4-benzoyl-3′, 5′-O-bis(4, 4′-dimethoxytrityl)-2′-deoxycytidine and the respective peak areas were 0.9%, 0.13%, and 1.8%, respectively, which indicates that the above procedure had no substantial effect on the purification.

Aufarbeitung

  1. filtrationA white precipitate was recovered by filtration
  2. washwas washed twice with water
  3. customwas dried at 50° C. in a vacuum

Quellen und Nachweise

ORD-Eintrag
ord-e9eafc1f87a845769be475d43c95b20e
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06936709B2

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