2',3',5'-tri-O-acetyladenosine → N6-(2-oxo-3,3-dimethoxy-4-chloro-5-pyrrolidinyl)adenosine 2',3',5'-triacetate

HRID 358014노트

반응식

HRID 358014 반응식
[CH3:1][O:2][C:3]1([O:12][CH3:13])[CH:7]([Cl:8])[CH:6](OC)[NH:5][C:4]1=[O:11].[C:14]([O:17][C@@H:18]1[C@H:22]([O:23][C:24](=[O:26])[CH3:25])[C@@H:21]([CH2:27][O:28][C:29](=[O:31])[CH3:30])[O:20][C@H:19]1[N:32]1[C:41]2[N:40]=[CH:39][N:38]=[C:36]([NH2:37])[C:35]=2[N:34]=[CH:33]1)(=[O:16])[CH3:15]>CCCCCC.CC(C)=O>[C:14]([O:17][C@@H:18]1[C@H:22]([O:23][C:24](=[O:26])[CH3:25])[C@@H:21]([CH2:27][O:28][C:29](=[O:31])[CH3:30])[O:20][C@H:19]1[N:32]1[C:41]2[N:40]=[CH:39][N:38]=[C:36]([NH:37][CH:6]3[NH:5][C:4](=[O:11])[C:3]([O:2][CH3:1])([O:12][CH3:13])[CH:7]3[Cl:8])[C:35]=2[N:34]=[CH:33]1)(=[O:16])[CH3:15]

참가 물질

4

반응물 2

HCID 965032',3',5'-tri-O-acetyladenosineHCID 129469943,3,5-Trimethoxy-4-chloro-2-pyrrolidinone

생성물 1

HCID 131713629N6-(2-oxo-3,3-dimethoxy-4-chloro-5-pyrrolidinyl)adenosine 2',3',5'-triacetate수율 63.2%

시약·촉매·용매 1

HCID 21880519Acetone hexane용매

실험 절차

3,3,5-Trimethoxy-4-chloro-2-pyrrolidinone (500 mg) was evenly admixed with adenosine 2',3',5'-triacetate (940 mg) and the mixture was melted and reacted at 170° C. for 1 hour. The reaction mixture was subjected to silica gel column chromatography using hexane-acetone (1:1) as the eluent to obtain N6 -(2-oxo-3,3-dimethoxy-4-chloro-5-pyrrolidinyl)adenosine 2',3',5'-triacetate (860 mg). This product was dissolved in ammonia-saturated methanol (40 ml) and allowed to stand at 5° C. for 15 hours, at the end of which time the solvent was distilled off. The residue was washed with chloroform and the insolubles were subjected to silica gel column chromatography using chloroform-methanol (10:1) as the eluent. The active fractions were pooled and concentrated under reduced pressure to give N6 -(2-oxo-3,3-dimethoxy-4-chloro-5-pyrrolidinyl)adenosine (590 mg).

후처리

  1. customreacted at 170° C. for 1 hour

출처 및 근거

ORD 기록
ord-d2864b25f8c94b69a3f25b068f5b9efc
출처 데이터셋
uspto-grants-1984_08
특허 번호
US04464361

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