Bromotrimethylsilane → HCID 86748521, compound

HRID 1440212Notes

Reaction equation

HRID 1440212 reaction equation
[CH3:1][S:2]([CH:5]1[CH:10]([C:11]2[CH:40]=[CH:39][CH:38]=[CH:37][C:12]=2[C:13]([N:15]([CH:34]=[N:35][NH2:36])[CH2:16][CH:17]([P:26]([O:31]CC)(=[O:30])[O:27]CC)[P:18]([O:23]CC)(=[O:22])[O:19]CC)=[O:14])[CH2:9][CH2:8][NH:7][CH2:6]1)(=[O:4])=[O:3].Br[Si](C)(C)C>O1CCOCC1.CO.O>[CH3:1][S:2]([CH:5]1[CH:10]([C:11]2[CH:40]=[CH:39][CH:38]=[CH:37][C:12]=2[C:13]([N:15]([CH:34]=[N:35][NH2:36])[CH2:16][CH:17]([P:18]([OH:22])(=[O:19])[OH:23])[P:26]([OH:31])(=[O:27])[OH:30])=[O:14])[CH2:9][CH2:8][NH:7][CH2:6]1)(=[O:4])=[O:3]

Participants

6

Reactant 2

HCID 76113BromotrimethylsilaneHCID 86748522HCID 86748522, compound

Product 1

HCID 86748521HCID 86748521, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

1.5 g (2.4 mmol) of tetraethyl 2-[(3-methylsulfonyl-4-piperidylbenzoyl)-(aminoiminomethyl) amino]ethane-1,1-bisphosphonate from Example 1 are dissolved in 60 ml of absolute dioxane at 60° C. The reaction mixture is subsequently allowed to reach room temperature, and 1.64 g (10.8 mmol) of bromotrimethylsilane are added. The mixture is stirred at room temperature for 16 hours and subsequently heated at 60° C. for a further 4 hours. Solvent and volatiles are subsequently removed at 40° C./0.1 torr. 15 ml of water are then added to the residue, and the mixture is stirred at room temperature for 4 hours. The resulting residue is filtered off and washed several times with ethanol. The residue resulting from this is subsequently boiled in 20 ml of methanol and 10 ml of water.

Workup

  1. customto reach room temperature
  2. temperaturesubsequently heated at 60° C. for a further 4 hours
  3. customSolvent and volatiles are subsequently removed at 40° C./0.1 torr
  4. addition15 ml of water are then added to the residue
  5. stirringthe mixture is stirred at room temperature for 4 hours
  6. filtrationThe resulting residue is filtered off
  7. washwashed several times with ethanol
  8. customThe residue resulting from

Sources & evidence

ORD record
ord-96bd2aa6a4844e949bd22ac05c88f0ec
Source dataset
uspto-grants-1996_03
Patent number
US05498617

Reaction notes

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