Diisopropylethylamine → 5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-cyanoethoxymethyl)uridine

HRID 1694672

반응식

HRID 1694672 반응식
[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

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 116654052-Cyanoethyl chloromethyl etherHCID 117633095'-O-(Bis(4-methoxyphenyl)phenylmethyl)uridine

생성물 1

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

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-35953b5aaac94f2fb0174fb4f50312d8
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158775B2

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