Chlorotrimethylsilane → HCID 137231708, compound

HRID 612838Notes

Reaction equation

HRID 612838 reaction equation
[CH2:1]([O:19][C@@H:20]1[C@H:24]([OH:25])[C@@H:23]([CH2:26][OH:27])[O:22][C@H:21]1[N:28]1[C:38]2[N:37]=[C:35]([NH2:36])[NH:34][C:32](=[O:33])[C:31]=2[N:30]=[CH:29]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C[Si](Cl)(C)C.[C:44](Cl)(=[O:48])[CH:45]([CH3:47])[CH3:46].[OH-].[NH4+:51]>N1C=CC=CC=1.O>[N:51]#[N:28].[C:44]([C@@:21]1([N:28]2[C:38]3[N:37]=[C:35]([NH2:36])[NH:34][C:32](=[O:33])[C:31]=3[N:30]=[CH:29]2)[O:22][C@H:23]([CH2:26][OH:27])[C@@H:24]([OH:25])[C@H:20]1[O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])(=[O:48])[CH:45]([CH3:47])[CH3:46]

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 14923Ammonium HydroxideHCID 62325Isobutyryl chlorideHCID 1355097442'-O-Octadecylguanosine

Product 1

HCID 137231708HCID 137231708, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

2'-O-Octadecylguanosine (1.9 g) in pyridine (150 ml) was cooled in an ice bath, and treated with trimethylsilyl chloride (2 g, 5 eq) and isobutyryl chloride (2 g, 5 eq). The reaction mixture was stirred for 4 hours, during which time it was allowed to warm to room temperature. The solution was cooled, water added (10 mL) and stirred for an additional 30 minutes. Concentrated ammonium hydroxide (10 mL) was added and the solution concentrated in vacuo. The residue was purified by silica gel chromatography (eluted with 3% MeOH/EtOAc) to yield 1.2 g of product.

Workup

  1. temperatureThe solution was cooled
  2. stirringstirred for an additional 30 minutes
  3. concentrationthe solution concentrated in vacuo
  4. customThe residue was purified by silica gel chromatography (eluted with 3% MeOH/EtOAc)

Sources & evidence

ORD record
ord-c75703ce435444d8941212ee0c74e61b
Source dataset
uspto-grants-1999_12
Patent number
US06005087

Reaction notes

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