Chlorotrimethylsilane → HCID 11146723, compound

HRID 1168581Notes

Reaction equation

HRID 1168581 reaction equation
[Si:1]([O:18][CH2:19][C@H:20]1[O:24][C@@H:23]([N:25]2[C:34]3[N:33]=[CH:32][N:31]=[C:29]([NH2:30])[C:28]=3[N:27]=[CH:26]2)[C@H:22]([O:35][CH2:36][CH2:37][OH:38])[C@@H:21]1[OH:39])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si](C)(C)Cl.[C:45](Cl)(=[O:52])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.[NH4+].[OH-]>N1C=CC=CC=1.CCOC(C)=O.O>[Si:1]([O:18][CH2:19][C@H:20]1[O:24][C@@H:23]([N:25]2[C:34]3[N:33]=[CH:32][N:31]=[C:29]([NH:30][C:45](=[O:52])[C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)[C:28]=3[N:27]=[CH:26]2)[C@H:22]([O:35][CH2:36][CH2:37][OH:38])[C@@H:21]1[OH:39])([C:14]([CH3:15])([CH3:17])[CH3:16])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

8

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 7412Benzoyl chlorideHCID 14923Ammonium HydroxideHCID 11307367HCID 11307367, compound

Product 1

HCID 11146723HCID 11146723, compoundYield 83.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dried 5′-O-t-butyldiphenylsilyl-2′-O-(hydroxyethyl)-adenosine (24 g, 43.7 mmol) was dissolved in anhydrous pyridine (500 mL) under inert atmosphere, and trimethylchlorosilane (27.7 mL, 218 mmol) was added at 0° C. The reaction was allowed to warm to ambient temperature, stirred for 1 hour, then cooled to 0° C. Benzoyl chloride (25.3 mL, 218 mmol) was added dropwise, then the reaction was allowed to warm to ambient temperature and stirred for 4 hours after which it was cooled to 0° C. and water (100 mL) was added. After stirring for 10 minutes aqueous 30% NH4OH (100 mL) was added, and the reaction was stirred at 0° C. for 1 hour. The solvent was evaporated in vacuo to give a residue which was dissolved in EtOAc (1 L), and the resulting solution was washed with water (200 mL) twice, then with brine (100 mL). The organic solution was dried with MgSO4, and the solvent was evaporated in vacuo to give a residue. The residue was purified by column chromatography using CH2Cl2-EtOAc-MeOH, 70:27:3, to give the title compound as a solid (23.77 g, 83%).

Workup

  1. additionwas added at 0° C
  2. temperaturecooled to 0° C
  3. temperatureto warm to ambient temperature
  4. stirringstirred for 4 hours after which it
  5. temperaturewas cooled to 0° C.
  6. additionwas added
  7. stirringthe reaction was stirred at 0° C. for 1 hour
  8. customThe solvent was evaporated in vacuo
  9. customto give a residue which
  10. washthe resulting solution was washed with water (200 mL) twice
  11. dry with materialThe organic solution was dried with MgSO4
  12. customthe solvent was evaporated in vacuo
  13. customto give a residue
  14. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-186052eecbcf44899ab880ffb3d6327f
Source dataset
uspto-grants-2003_09
Patent number
US06624294B2

Reaction notes

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