Bromotrimethylsilane → HCID 13231988, compound

HRID 1648952Notes

Reaction equation

HRID 1648952 reaction equation
C[Si](Br)(C)C.[OH:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[C:9](=[O:40])[CH:10]=[C:11]([C:18]1[C:36]([O:37][CH3:38])=[CH:35][C:34]([CH3:39])=[CH:33][C:19]=1[C:20]([NH:22][CH:23]([P:25](=[O:32])([O:29]CC)[O:26]CC)[CH3:24])=[O:21])[C:12]2=[O:17]>>[OH:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[C:9](=[O:40])[CH:10]=[C:11]([C:18]1[C:36]([O:37][CH3:38])=[CH:35][C:34]([CH3:39])=[CH:33][C:19]=1[C:20]([NH:22][CH:23]([P:25](=[O:26])([OH:29])[OH:32])[CH3:24])=[O:21])[C:12]2=[O:17]

Participants

3

Reactant 2

HCID 76113BromotrimethylsilaneHCID 13231987HCID 13231987, compound

Product 1

HCID 13231988HCID 13231988, compoundYield 45%

Procedure

Trimethylsilyl bromide was added to diethyl 1-[2-(5-hydroxy-1,4-naphthoquinon-2-yl)-3-methoxy-5-methylbenzamido]ethylphosphonate (500 mg) as obtained in Example 9 and the mixture was stirred at room temperature for 2 hours. The excess trimethylsilyl bromide was distilled off, water was added to the residue, and the mixture was stirred at room temperature for 30 minutes. The resultant crude crystals were recovered by filtration and recrystallized from methanol. The above procedure gave yellow crystals (200 mg) of 1-[2-(5-hydroxy-1,4-naphthoquinon-2-yl)-3-methoxy-5-methylbenzamido]ethylphosphonic acid.

Workup

  1. customas obtained in Example 9
  2. distillationThe excess trimethylsilyl bromide was distilled off
  3. additionwater was added to the residue
  4. stirringthe mixture was stirred at room temperature for 30 minutes
  5. filtrationThe resultant crude crystals were recovered by filtration
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-82a4a49e05e1488eb5aaad7d21bfcace
Source dataset
uspto-grants-1983_11
Patent number
US04414226

Reaction notes

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