Chlorotrimethylsilane → HCID 53790515, compound

HRID 650221Notes

Reaction equation

HRID 650221 reaction equation
[CH3:1][O:2][C@@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]1[O:9][C@@H:10]1[C@H:14]([OH:15])[C@@H:13]([CH2:16][OH:17])[O:12][C@H:11]1[N:18]1[C:27]2[N:26]=[CH:25][N:24]=[C:22]([NH2:23])[C:21]=2[N:20]=[CH:19]1.C[Si](Cl)(C)C.[C:33](Cl)(=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[OH-].[NH4+]>N1C=CC=CC=1.O>[C:33]([NH:23][C:22]1[C:21]2[N:20]=[CH:19][N:18]([C:27]=2[N:26]=[CH:25][N:24]=1)[C@@H:11]1[O:12][C@H:13]([CH2:16][OH:17])[C@@H:14]([OH:15])[C@H:10]1[O:9][C@@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@H:3]1[O:2][CH3:1])(=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 7412Benzoyl chlorideHCID 14923Ammonium HydroxideHCID 18719640HCID 18719640, compound

Product 1

HCID 53790515HCID 53790515, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent2×

Conditions

Temperature
5 °C

Procedure

A solution of 2′-O-(trans-2-methoxy-cyclohexyl) adenosine (0.056 mol) in pyridine (100 mL) is evaporated under reduced pressure to dryness. The residue is redissolved in pyridine (560 mL) and cooled in an ice water bath. Trimethylsilyl chloride (36.4 mL, 0.291 mol) is added and the reaction is stirred at 5° C. for 30 minutes. Benzoyl chloride (33.6 mL, 0.291 mol) is added and the reaction is allowed to warm to 25° C. for 2 hours and then cooled to 5° C. The reaction is diluted with cold water (112 mL) and after stirring for 15 min, concentrated ammonium hydroxide (112 mL). After 30 min, the reaction is concentrated under reduced pressure (below 30° C.) followed by coevaporation with toluene (2×100 mL). The residue is dissolved in ethyl acetate-methanol (400 mL, 9:1) and the undesired silyl by-products are removed by filtration. The filtrate is concentrated under reduced pressure and purified by silica gel flash column chromatography (800 g, chloroform-methanol 9:1). Selected fractions are combined, concentrated under reduced pressure and dried at 25°C./0.2 mmHg for 2 h to give the title compound.

Workup

  1. temperaturecooled in an ice water bath
  2. temperatureto warm to 25° C. for 2 hours
  3. temperaturecooled to 5° C
  4. stirringafter stirring for 15 min
  5. waitAfter 30 min
  6. concentrationthe reaction is concentrated under reduced pressure (below 30° C.)
  7. dissolutionThe residue is dissolved in ethyl acetate-methanol (400 mL, 9:1)
  8. customthe undesired silyl by-products are removed by filtration
  9. concentrationThe filtrate is concentrated under reduced pressure
  10. custompurified by silica gel flash column chromatography (800 g, chloroform-methanol 9:1)
  11. concentrationconcentrated under reduced pressure
  12. customdried at 25°C./0.2 mmHg for 2 h

Sources & evidence

ORD record
ord-3712d0ca7714493fa359475a1cb964f9
Source dataset
uspto-grants-2001_08
Patent number
US06271358B1

Reaction notes

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