2',3',5'-tri-O-acetyladenosine → N6-(5-oxo-2-pyrrolidinyl)adenosine 2',3',5'-triacetate

HRID 358009노트

반응식

HRID 358009 반응식
[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[O:7][C@H:6]1[N:19]1[C:28]2[N:27]=[CH:26][N:25]=[C:23]([NH2:24])[C:22]=2[N:21]=[CH:20]1)(=[O:3])[CH3:2].C(O[CH:32]1[NH:36][C:35](=[O:37])[CH2:34][CH2:33]1)C>CN(C)C=O>[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[O:7][C@H:6]1[N:19]1[C:28]2[N:27]=[CH:26][N:25]=[C:23]([NH:24][CH:32]3[CH2:33][CH2:34][C:35](=[O:37])[NH:36]3)[C:22]=2[N:21]=[CH:20]1)(=[O:3])[CH3:2]

참가 물질

4

반응물 2

HCID 965032',3',5'-tri-O-acetyladenosineHCID 35805555-Ethoxy-2-pyrrolidinone

생성물 1

HCID 13109688N6-(5-oxo-2-pyrrolidinyl)adenosine 2',3',5'-triacetate수율 90.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Adenosine 2',3',5'-triacetate (2.0 g) and 5-ethoxy-2-pyrrolidinone (1.2 g) were stirred in N,N-dimethylformamide (10 ml) at 130° C. overnight. The reaction mixture was distilled to remove the N,N-dimethylformamide and the residue was subjected to silica gel column chromatography using chloroformacetone (5:3) as the eluent. The active fractions were pooled and concentrated under reduced pressure to give N6 -(5-oxo-2-pyrrolidinyl)adenosine 2',3',5'-triacetate as an oil (2.2 g).

후처리

  1. distillationThe reaction mixture was distilled
  2. customto remove the N,N-dimethylformamide
  3. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-cf2ea343da54445997c69de70ffc7bbe
출처 데이터셋
uspto-grants-1984_08
특허 번호
US04464361

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