Bromotrimethylsilane → HCID 54527323, compound

HRID 376162Notes

Reaction equation

HRID 376162 reaction equation
C([O:4][CH:5]([CH3:29])[CH2:6][C:7]([CH2:18][P:19]([O:25]C(C)C)([O:21]C(C)C)=[O:20])=[CH:8][CH:9]([NH:15]C=O)[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=O)C.C[Si](C)(C)Br>C(O)C>[NH2:15][CH:9]([CH:8]=[C:7]([CH2:18][P:19]([OH:25])([OH:21])=[O:20])[CH2:6][CH:5]([OH:4])[CH3:29])[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 53768570HCID 53768570, compound

Product 1

HCID 54527323HCID 54527323, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

11.5 g (26.4 mmol) of ethyl 6-acetoxy-2-formylamino-4-diisopropylphosphonomethyl-hept-3-enoate are dissolved in 70 ml of abs. CH2C12 and to this solution are added 13.7 ml (105.6 mmol) of trimethylbromosilane. The reaction mixture is allowed to stand for 24 hours at room temperature and, after addition of 70 ml of abs. ethanol, allowed to stand again for 24 hours. The reaction mixture is concentrated by evaporation and the residue is dissolved in 70 ml of ethanol. A mixture of 70 ml of propylene oxide and 70 ml of ethanol is then added dropwise. The white suspension so obtained is stirred for 30 minutes at room temperature and for 30 minutes at 0° C. and then filtered with suction. The filter product is dried giving white crystals of ethyl 2-amino-6-hydroxy-4-phosphonomethyl-hept-3-enoate with a melting point of 211°-212° C. (decomp.).

Workup

  1. additionafter addition of 70 ml of abs
  2. waitto stand again for 24 hours
  3. concentrationThe reaction mixture is concentrated by evaporation
  4. dissolutionthe residue is dissolved in 70 ml of ethanol
  5. additionA mixture of 70 ml of propylene oxide and 70 ml of ethanol
  6. additionis then added dropwise
  7. customThe white suspension so obtained
  8. filtrationfiltered with suction
  9. customThe filter product is dried

Sources & evidence

ORD record
ord-851ad8de4d814f40b857e56e9104ac9f
Source dataset
uspto-grants-1996_01
Patent number
US05488140

Reaction notes

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