Bromotrimethylsilane → HCID 86748521, compound

HRID 2258532Notes

Reaction equation

HRID 2258532 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

Conditions

Temperature
60 °C

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

Sources & evidence

ORD record
ord-510179ebe27941e88d1a853cc21c4d3a
Source dataset
uspto-grants-1997_08
Patent number
US05661174

Reaction notes

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