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

HRID 586766

반응식

HRID 586766 반응식
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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-e9eafc1f87a845769be475d43c95b20e
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06936709B2

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