Sodium Azide → HCID 15516178, compound

HRID 351994Notes

Reaction equation

HRID 351994 reaction equation
[CH3:1][O:2][C:3]1[CH:52]=[CH:51][C:6]([C:7]([O:22][CH2:23][C@H:24]2[O:28][C@@H:27]([N:29]3[CH:37]=[C:35]([CH3:36])[C:33](=[O:34])[NH:32][C:30]3=[O:31])[CH2:26][C@:25]2([CH2:39]OS(C2C=CC(C)=CC=2)(=O)=O)[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.[N-:53]=[N+:54]=[N-:55].[Na+]>CN(C=O)C.CCOC(C)=O>[CH3:15][O:14][C:11]1[CH:10]=[CH:9][C:8]([C:7]([O:22][CH2:23][C@H:24]2[O:28][C@@H:27]([N:29]3[CH:37]=[C:35]([CH3:36])[C:33](=[O:34])[NH:32][C:30]3=[O:31])[CH2:26][C@:25]2([CH2:39][N:53]=[N+:54]=[N-:55])[OH:38])([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:52][CH:51]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 15405112HCID 15405112, compound

Product 1

HCID 15516178HCID 15516178, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A slurry of 5′-O-(4,4′-dimethoxytrityl)-3′-p-toluensulfonyloxymethylthymidine (0.40 g; 0.55 mmol) and NaN3 (0.11 g; 1.65 mmol) in anhydrous DMF (3 ml) was heated at 50° C. for 3 days. The reaction mixture was cooled to room temperature, diluted with EtOAc (30 ml), and washed with water (3×40 ml), then with 10% NaHCO3 (3×40 ml). The organic layer was dried over Na2SO4, concentrated and purified by chromatography on silica (EtOAc-Hexanes, 1:1) to yield 0.30 g (92%) of 5′-O-(4,4′-dimethoxytrityl)-3′-C-azidomethylthymidine as a colorless powder.

Workup

  1. washwashed with water (3×40 ml)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. custompurified by chromatography on silica (EtOAc-Hexanes, 1:1)

Sources & evidence

ORD record
ord-305cf1a885fb49458fa3714553b26996
Source dataset
uspto-grants-2004_06
Patent number
US06743902B1

Reaction notes

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