HCID 10941510, compound → HCID 11826621, compound

HRID 1168582Notes

Reaction equation

HRID 1168582 reaction equation
[Si]([O:18][CH2:19][C@H:20]1[O:24][C@@H:23]([N:25]2[C:42]3[N:41]=[CH:40][N:39]=[C:29]([NH:30][C:31](=[O:38])[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[C:28]=3[N:27]=[CH:26]2)[C@H:22]([O:43][CH2:44][CH2:45][O:46][N:47]([CH3:49])[CH3:48])[C@@H:21]1[OH:50])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>C1COCC1>[C:31]([NH:30][C:29]1[C:28]2[N:27]=[CH:26][N:25]([C:42]=2[N:41]=[CH:40][N:39]=1)[C@@H:23]1[O:24][C@H:20]([CH2:19][OH:18])[C@@H:21]([OH:50])[C@H:22]1[O:43][CH2:44][CH2:45][O:46][N:47]([CH3:49])[CH3:48])(=[O:38])[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

3

Reactant 1

HCID 10941510HCID 10941510, compound

Product 1

HCID 11826621HCID 11826621, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5′-O-t-Butyldiphenylsilyl-N6-benzoyl-2′-O-(dimethylaminooxyethyl)adenosine (7.77 g, 11.15 mmol) was dissolved in THF (110 mL), and tetrabutylammonium fluoride (TBAF)on silica (1.0-1.5 mmol/g silica, 10.1 g) was added. After stirring for 24 hours the solid was filtered, washed with THF, and the solvent was evaporated in vacuo to give a solid which was purified by column chromatography using CH2Cl2-EtOAc-MeOH, 75:20:5, to give the title compound as a solid (4.42 g, 86%).

Workup

  1. filtrationwas filtered
  2. washwashed with THF
  3. customthe solvent was evaporated in vacuo
  4. customto give a solid which
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-83346362f8f444aaa7bec4bb1d44c780
Source dataset
uspto-grants-2003_09
Patent number
US06624294B2

Reaction notes

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