Diisopropylethylamine → 4-N-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-cyanoethoxymethyl)cytidine

HRID 1694674

反応式

HRID 1694674 の反応式
[C:1]([NH:4][C:5]1[CH:42]=[CH:41][N:8]([C@@H:9]2[O:40][C@H:14]([CH2:15][O:16][C:17]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=3)[C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[C@@H:12]([OH:13])[C@H:10]2[OH:11])[C:7](=[O:43])[N:6]=1)(=[O:3])[CH3:2].C(N(C(C)C)CC)(C)C.[C:53]([CH2:55][CH2:56][O:57][CH2:58]Cl)#[N:54].C(=O)(O)[O-].[Na+]>ClCCCl>[C:1]([NH:4][C:5]1[CH:42]=[CH:41][N:8]([C@@H:9]2[O:40][C@H:14]([CH2:15][O:16][C:17]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=3)[C:18]3[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=3)[C@@H:12]([OH:13])[C@H:10]2[O:11][CH2:58][O:57][CH2:56][CH2:55][C:53]#[N:54])[C:7](=[O:43])[N:6]=1)(=[O:3])[CH3:2]

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 10929984N-(1-((2R,3R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3,4-dihydroxytetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)acetamideHCID 116654052-Cyanoethyl chloromethyl ether

生成物 1

HCID 866307224-N-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-cyanoethoxymethyl)cytidine収率 35%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

N4-Acetyl-5′-O-(4,4′-dimethoxytrityl)cytidine (588 mg, 1 mmol) was dissolved in 4 mL of 1,2-dichloroethane, and 452 mg of diisopropylethylamine (3.5 mmol) was added thereto, and then 365 mg of dibutylstannyl dichloride (1.2 mmol) was further added. The reaction was performed at room temperature for 1 hour. Then, the reaction was performed at 80° C., and 155.4 mg of chloromethyl 2-cyanoethyl ether (1.3 mmol) was added dropwise, and the solution was stirred for 60 minutes. After the reaction completed, the reaction solution was added into an aqueous saturated sodium bicarbonate solution, and was extracted with methylene chloride. 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 N4-acetyl-5′-O-(4,4′-dimethoxytrityl)-2′-O-(2-cyanoethoxymethyl) cytidine (219 mg, yield 35%).

後処理

  1. customwas performed at 80° C.
  2. extractionwas extracted 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

出典と根拠

ORDレコード
ord-43d9a27bf16a4ed081b46b9d34773886
出典データセット
uspto-grants-2012_04
特許番号
US08158775B2

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