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Pyridine → N6-Benzoyladenosine

HRID 2082276
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인쇄 미리보기

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HRID 2082276 반응식
C([CH:9]([OH:59])[C@@:10]1(C(=O)C2C=CC=CC=2)[O:14][C@@:13](C(=O)C2C=CC=CC=2)([N:15]2[C:24]3[N:23]=[CH:22][N:21]=[C:19]([NH2:20])[C:18]=3[N:17]=[CH:16]2)[C@:12](C(=O)C2C=CC=CC=2)([OH:33])[C@:11]1(C(=O)C1C=CC=CC=1)[OH:42])(=O)C1C=CC=CC=1.C[O-:61].[Na+].[NH+]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1.N1[CH:74]=[CH:73]C=CC=1>CO.O>[C:64]([NH:20][C:19]1[C:18]2[N:17]=[CH:16][N:15]([C:24]=2[N:23]=[CH:22][N:21]=1)[C@@H:13]1[O:14][C@H:10]([CH2:9][OH:59])[C@@H:11]([OH:42])[C@H:12]1[OH:33])(=[O:61])[C:65]1[CH:74]=[CH:73][CH:68]=[CH:67][CH:66]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 1049PyridineHCID 4989215PyridiniumHCID 10942334Sodium MethoxideHCID 131717784HCID 131717784, 화합물

생성물 1

HCID 11728391N6-Benzoyladenosine수율 83%

시약·촉매·용매 2

HCID 887Methanol용매
HCID 962
Water
용매

실험 절차

A solution of 7.88 g (10 mmole) of the pentabenzoyl adenosine (1A) in 150 ml dry pyridine and 50 ml dry MeOH was treated with 50 ml 1M sodium methylate solution. After 15 min the solution was poured onto an ice cold solution of a 110 ml DOWEX ion exchanger 50×4 (pyridinium form) in ca 20 ml water. After 5 h stirring the pH was 5.5-6.0. After filtering from the ion exchanger, the residue was washed with boiling MeOH/water (3/1). The filtrate was evaporated to dryness and crystallized from MeOH/water 2/1 to give 3.25 g (83%) of the product as colorless needles, m.p. 151°-153° C.

후처리

  1. filtrationAfter filtering from the ion exchanger
  2. washthe residue was washed with boiling MeOH/water (3/1)
  3. customThe filtrate was evaporated to dryness
  4. customcrystallized from MeOH/water 2/1

출처 및 근거

ORD 기록
ord-3dc3f3847fa04fed91be4c89f0b257df
출처 데이터셋
uspto-grants-1993_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05188897

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