Bromotrimethylsilane → HCID 70091067, compound

HRID 1637219Notes

Reaction equation

HRID 1637219 reaction equation
C([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)C.C[Si](Br)(C)C.[NH4+].[OH-].O>C(Cl)(Cl)Cl>[NH:33]1[CH2:34][CH2:35][CH:30]([CH2:29][CH2:28][CH2:27][CH2:26][O:25][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH2:18][CH2:17][CH2:16][CH2:15][S:12]([NH:11][CH2:10][CH2:9][P:4]([OH:8])(=[O:3])[OH:5])(=[O:14])=[O:13])[CH2:31][CH2:32]1

Participants

5

Reactant 3

HCID 76113BromotrimethylsilaneHCID 86589665Water ammonium hydroxideHCID 86751156HCID 86751156, compound

Product 1

HCID 70091067HCID 70091067, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 6-9 (0.63 g, 0.142 mmol) in CHCl3 (5 ml) at rt was treated with TMSBr (0.85 mmol) for 16 hrs. The solvent was removed and the residue was dissolved in 10% aqueous acetone and this stripped to dryness. The residue was mixed with toluene and the resulting gum was purified by flash chromatography on silica gel eluting with 4:1:1 HtOH/H2O/NH4OH to provide pure 6-11. Rf 0.38 (silica gel, 4:1:1 HtOH/NH4OH/H2O.

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue was dissolved in 10% aqueous acetone
  3. additionThe residue was mixed with toluene
  4. customthe resulting gum was purified by flash chromatography on silica gel eluting with 4:1:1 HtOH/H2O/NH4OH
  5. customto provide pure 6-11

Sources & evidence

ORD record
ord-94be56c65fce4476a9537b1a6072065b
Source dataset
uspto-grants-2000_03
Patent number
US06040317

Reaction notes

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