N,N-二异丙基乙胺 → 5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-cyanoethoxymethyl)uridine

HRID 1694672

反应方程式

HRID 1694672 反应方程式
[CH3:1][O:2][C:3]1[CH:40]=[CH:39][C:6]([C:7]([O:22][CH2:23][C@H:24]2[O:28][C@@H:27]([N:29]3[CH:36]=[CH:35][C:33](=[O:34])[NH:32][C:30]3=[O:31])[C@H:26]([OH:37])[C@@H:25]2[OH:38])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.[C:50]([CH2:52][CH2:53][O:54][CH2:55]Cl)#[N:51].C(=O)(O)[O-].[Na+]>ClCCCl>[CH3:15][O:14][C:11]1[CH:12]=[CH:13][C:8]([C:7]([O:22][CH2:23][C@H:24]2[O:28][C@@H:27]([N:29]3[CH:36]=[CH:35][C:33](=[O:34])[NH:32][C:30]3=[O:31])[C@H:26]([O:37][CH2:55][O:54][CH2:53][CH2:52][C:50]#[N:51])[C@@H:25]2[OH:38])([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:6]2[CH:39]=[CH:40][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:9][CH:10]=1

参与物

6

反应物 4

HCID 81531N,N-二异丙基乙胺HCID 516892碳酸氢钠HCID 116654052-Cyanoethyl chloromethyl etherHCID 117633095'-O-(4,4'-二甲氧基三苯甲基)尿苷

产物 1

HCID 672792965'-O-(4,4'-dimethoxytrityl)-2'-O-(2-cyanoethoxymethyl)uridine收率 34%

试剂、催化剂与溶剂 1

HCID 111,2-二氯乙烷溶剂

实验过程

5′-O-(4,4′-Dimethoxytrityl)uridine (546 mg, 1 mmol) was dissolved in 4 mL of 1,2-dichloroethane, and 452 mg of diisopropylethylamine (3.5 mmol) was added thereto, and 365 mg of dibutylstannyl dichloride (1.2 mmol) was further added thereto. The reaction was performed at room temperature for 1 hour. Subsequently, the reaction was performed at 80° C., and 155.4 mg of chloromethyl 2-cyanoethyl ether (1.3 mmol) was added dropwise, and the reaction solution was stirred for 30 minutes. After the reaction completed, the reaction solution was added into an aqueous saturated sodium bicarbonate solution, and was subjected to extraction with methylene chloride, and the extract was dried over anhydrous magnesium sulfate, and the solvent was distilled off. The obtained mixture was purified by 30 g of silica gel column chromatography to obtain 5′-O-(4,4′-dimethoxytrityl)-2′-O-(2-cyanoethoxymethyl)uridine (197 mg, yield 34%).

后处理

  1. customwas performed at 80° C.
  2. extractionwas subjected to extraction with methylene chloride
  3. dry with materialthe extract was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customThe obtained mixture was purified by 30 g of silica gel column chromatography

来源与证据

ORD记录
ord-35953b5aaac94f2fb0174fb4f50312d8
来源数据集
uspto-grants-2012_04
专利号
US08158775B2

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