Diisopropylethylamine → 6-N-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-cyanoethoxymethyl)adenosine

HRID 1694677

Reaction equation

HRID 1694677 reaction equation
[C:1]([NH:4][C:5]1[C:6]2[N:7]=[CH:8][N:9]([C:42]=2[N:43]=[CH:44][N:45]=1)[C@@H:10]1[O:41][C@H:15]([CH2:16][O:17][C:18]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[C@@H:13]([OH:14])[C@H:11]1[OH:12])(=[O:3])[CH3:2].C(N(C(C)C)CC)(C)C.[C:55]([CH2:57][CH2:58][O:59][CH2:60]Cl)#[N:56].C(=O)(O)[O-].[Na+]>ClCCCl>[C:1]([NH:4][C:5]1[C:6]2[N:7]=[CH:8][N:9]([C:42]=2[N:43]=[CH:44][N:45]=1)[C@@H:10]1[O:41][C@H:15]([CH2:16][O:17][C:18]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)([C:19]2[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=2)[C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[C@@H:13]([OH:14])[C@H:11]1[O:12][CH2:60][O:59][CH2:58][CH2:57][C:55]#[N:56])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 116654052-Cyanoethyl chloromethyl etherHCID 71356814Adenosine, N-acetyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-

Product 1

HCID 866307246-N-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-cyanoethoxymethyl)adenosineYield 33%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

N6-Acetyl-5′-O-(4,4′-dimethoxytrityl)adenosine (22.0 g, 36.0 mmol) was dissolved in 170 mL of 1,2-dichloroethane, and 16.3 g of diisopropylethylamine (126 mmol) was added, and 12.1 g of dibutylstannyl dichloride (39.7 mmol) was added subsequently. Then, the reaction was performed at room temperature for 1 hour. Then, the reaction solution was heated up to 80° C., and 4.30 g of chloromethyl 2-cyanoethyl ether (36.0 mmol) was added dropwise, and the solution was stirred for 30 minutes. After the reaction completed, the reaction solution was added to an aqueous saturated sodium bicarbonate solution, and was subjected to extraction with methylene chloride. The extract was dried over anhydrous magnesium sulfate, and the solvent was distilled off. The obtained mixture was purified by silica gel column chromatography to obtain N6-acetyl-5′-O-(4,4′-dimethoxytrityl)-2′-O-(2-cyanoethoxymethyl) adenosine (7.47 g, yield 33%).

Workup

  1. extractionwas subjected to extraction with methylene chloride
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off
  4. customThe obtained mixture was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-41417203306d4df692589c32184f1708
Source dataset
uspto-grants-2012_04
Patent number
US08158775B2

Linked notes

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