Chlorotrimethylsilane → HCID 14134455, compound

HRID 1885137Notes

Reaction equation

HRID 1885137 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-2f22083b30584f5683f8fcea8cc23950
Source dataset
uspto-grants-1992_09
Patent number
US05143908

Reaction notes

Loading…