HCID 10632308, compound → HCID 20716774, compound

HRID 1250123Notes

Reaction equation

HRID 1250123 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C@@H:8]1[C@H:12]([OH:13])[C@@H:11]([CH2:14][O:15][C:16]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[O:10][C@H:9]1[N:39]1[C:48]2[N:47]=[CH:46][N:45]=[C:43]([NH2:44])[C:42]=2[N:41]=[CH:40]1.[C:49]([CH2:51][CH2:52][O:53][C:54](ON1C(=O)CCC1=O)=[O:55])#[N:50]>CC#N.CCOC(C)=O>[C:49]([CH2:51][CH2:52][O:53][C:54]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C@@H:8]1[C@H:12]([OH:13])[C@@H:11]([CH2:14][O:15][C:16]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:25]2[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=2)[C:17]2[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)[O:10][C@H:9]1[N:39]1[C:48]2[N:47]=[CH:46][N:45]=[C:43]([NH2:44])[C:42]=2[N:41]=[CH:40]1)=[O:55])#[N:50]

Participants

5

Reactant 2

HCID 10632308HCID 10632308, compoundHCID 20716771HCID 20716771, compound

Product 1

HCID 20716774HCID 20716774, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2′-O-(5-aminopentyl)-5′-O-(4,4′-dimethoxytrityl)-adenosine (1.0 g, 1.52 mmol) in anhydrous CH3CN (8.0 mL) was added with stirring, under argon, N-(2-Cyanoethoxycarbonyl)oxy succinimide (0.43 g, 2.02 mmol) After stirring for 5 h at room temperature the reaction mixture was diluted with EtOAc (50 mL) and washed with aq saturated bicarbonate (3×20 mL) and water (20 mL), dried (Na2SO4) and evaporated to give 53 as a light yellow foam (1.1 g, 98% yield). This compound was used without further purification for the next step.

Workup

  1. washwashed with aq saturated bicarbonate (3×20 mL) and water (20 mL)
  2. dry with materialdried (Na2SO4)
  3. customevaporated

Sources & evidence

ORD record
ord-c5b058571834477abf774fdc12f7f88d
Source dataset
uspto-grants-2002_01
Patent number
US06335434B1

Reaction notes

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