Chlorotrimethylsilane → HCID 14134455, compound

HRID 2372558Notes

Reaction equation

HRID 2372558 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([P:14]([OH:16])[OH:15])[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.C[Si](Cl)(C)C.Br[CH2:30][C:31](=[CH2:36])[C:32]([O:34][CH3:35])=[O:33]>C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][CH:12]([P:14]([CH2:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH2:30])(=[O:15])[OH:16])[CH3:13])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 5210932-Propenoic acid, 2-(bromomethyl)-, methyl esterHCID 19880129HCID 19880129, compound

Product 1

HCID 14134455HCID 14134455, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2.25 g (9.3 mmol) of 1-(benzyloxycarbonylamino)ethylphosphonous acid in 70 ml of methylene chloride, were added triethylamine (2.87 ml, 20 mmol), trimethylsilyl chloride (2.60 ml, 20 mmol), and methyl 2-bromomethylacrylate (1.66 g, 9.3 mmol) at 0° C. After stirring at room temperature for 20 hours, the reaction mixture was washed with H2O, 2N HCl, and then saturated NaCl solution and dried over anhydrous magnesium sulfate. The mixture obtained by filtration and evaporation was purified by silica gel chromatography (eluted with chloroform followed by 10% methanol-chloroform) to give 2.50 g (yield 79%) of the product.

Workup

  1. washthe reaction mixture was washed with H2O, 2N HCl
  2. dry with materialsaturated NaCl solution and dried over anhydrous magnesium sulfate
  3. customThe mixture obtained by filtration and evaporation
  4. customwas purified by silica gel chromatography (eluted with chloroform followed by 10% methanol-chloroform)

Sources & evidence

ORD record
ord-934512437ffd42a2b178c5e65be9c207
Source dataset
uspto-grants-1992_03
Patent number
US05099063

Reaction notes

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