Chlorotrimethylsilane → HCID 15009334, compound

HRID 1494501Notes

Reaction equation

HRID 1494501 reaction equation
[CH2:1]=[C:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[CH:17]=[CH:16][C:14]([NH2:15])=[N:13][C:11]1=[O:12].C[Si](Cl)(C)C.[C:23](Cl)(=[O:33])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].O.N>N1C=CC=CC=1.O>[CH2:1]=[C:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[CH:17]=[CH:16][C:14]([NH:15][C:23](=[O:33])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[N:13][C:11]1=[O:12]

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 66982Decanoyl chlorideHCID 3005913119804-96-5HCID 12896473Azane;hydrate

Product 1

HCID 15009334HCID 15009334, compoundYield 45.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

2'-Deoxy-2'-methylidenecytidine, 239 mg, was dissolved in 5 ml of pyridine, and to the solution was added dropwise 0.63 ml of trimethylsilyl chloride under ice cooling. The mixture was stirred at room temperature for 5 minutes and then 0.83 ml of decanoyl chloride was added dropwise to the mixture under ice cooling, followed by stirring at room temperature for 2 hours. After the reaction, 2 ml of water was added to the reaction solution, stirring was conducted at room temperature for 5 minutes, and then 2 ml of concentrated ammonia water was added to the solution, followed by stirring for 15 minutes. After the reaction, the solution was partitioned with chloroform, and the chloroform layer was distilled off under reduced pressure. The residue was treated with a silica gel chromatography (elution solvent-chloroform: methanol=25:1) to give 179 mg of the objective compound as an oleaginous product. Yield: 45.6%

Workup

  1. stirringby stirring at room temperature for 2 hours
  2. additionwas added to the reaction solution
  3. stirringstirring
  4. waitwas conducted at room temperature for 5 minutes
  5. stirringby stirring for 15 minutes
  6. customAfter the reaction
  7. customthe solution was partitioned with chloroform
  8. distillationthe chloroform layer was distilled off under reduced pressure
  9. additionThe residue was treated with a silica gel chromatography (elution solvent-chloroform: methanol=25:1)

Sources & evidence

ORD record
ord-209b11fcc276493abc54ec56062d5f24
Source dataset
uspto-grants-1991_06
Patent number
US05026835

Reaction notes

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