Bromotrimethylsilane → HCID 86751155, compound

HRID 1417975Notes

Reaction equation

HRID 1417975 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][CH2:10][NH:11][S:12]([CH2:15][CH2:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH:30]1[CH2:35][CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32][CH2:31]1)(=[O:14])=[O:13])(=[O:8])[O:5]CC)[CH3:2].C[Si](Br)(C)C>C(Cl)Cl>[CH2:1]([O:3][P:4]([CH2:9][CH2:10][NH:11][S:12]([CH2:15][CH2:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH:30]1[CH2:31][CH2:32][NH:33][CH2:34][CH2:35]1)(=[O:13])=[O:14])(=[O:5])[OH:8])[CH3:2]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 86751156HCID 86751156, compound

Product 1

HCID 86751155HCID 86751155, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-9 (0.09 g, 0.142 mmol) in CH2Cl2 cooled to 0° was treated with TMSBr (0.054, 0.355 mmol) and the resulting solution was stirred at rt for 16 hours with cooling. Et2N (100 μl) was added and the solvent was removed. The residue was dissolved in 10% aqueous acetone (5 ml), concentrated, and suspended in toluene to give a solid. This was purified by flash chromatography on silica gel eluting with 10:1:1 EtOH/H2O/NH4OH to give pure 6-10.

Workup

  1. temperaturewith cooling
  2. additionEt2N (100 μl) was added
  3. customthe solvent was removed
  4. dissolutionThe residue was dissolved in 10% aqueous acetone (5 ml)
  5. concentrationconcentrated
  6. customto give a solid
  7. customThis was purified by flash chromatography on silica gel eluting with 10:1:1 EtOH/H2O/NH4OH
  8. customto give pure 6-10

Sources & evidence

ORD record
ord-5486bac3514945f4b48b28360181b3a4
Source dataset
uspto-grants-1999_03
Patent number
US05880136

Reaction notes

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