Ethanol → HCID 3035775, compound

HRID 1682324Notes

Reaction equation

HRID 1682324 reaction equation
C[Si](C)(C)Br.[CH2:6]([O:8][C:9](=[O:28])[C@H:10]([NH:25]C=O)[CH:11]=[C:12]([CH3:24])[CH2:13][P:14]([O:20]C(C)C)([O:16]C(C)C)=[O:15])[CH3:7].C(O)C>ClCCl>[CH2:6]([O:8][C:9](=[O:28])[C@H:10]([NH2:25])[CH:11]=[C:12]([CH3:24])[CH2:13][P:14]([OH:16])([OH:20])=[O:15])[CH3:7]

Participants

5

Reactant 3

HCID 702EthanolHCID 76113BromotrimethylsilaneHCID 54446924HCID 54446924, compound

Product 1

HCID 3035775HCID 3035775, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

23 ml of trimethylbromosilane are added dropwise at room temperature within a period of 15 minutes to a solution of 10.3 g of 4 according to b) in 42 ml of dichloromethane. After 211/2 hours, 42 ml of ethanol are added while cooling with ice, and the mixture is stirred for 20 hours. The whole is then concentrated by evaporation and the residue is dissolved three times in 70 ml of toluene each time and in each case is concentrated by evaporation again. The residue is dissolved in 42 ml of ethanol, and 42 ml of propylene oxide are added. After 11/2 hours, the mixture is filtered. Drying the filtration residue in a vacuum desiccator over P2O5 /KOH (3 hours/80°) yields 6.17 g of 5; [α]D =-78° (c=0.6, H2O); m p. 194°-197° (decomp.), C8H16NO5P; calculated: C 40.51 %, H 6.80%, N 5.91%, P 13.06%; found: C 39.4%, H 7.09%, N 5.73%, P 12.98%.

Workup

  1. temperaturewhile cooling with ice
  2. concentrationThe whole is then concentrated by evaporation
  3. dissolutionthe residue is dissolved three times in 70 ml of toluene each time
  4. concentrationin each case is concentrated by evaporation again
  5. dissolutionThe residue is dissolved in 42 ml of ethanol
  6. addition42 ml of propylene oxide are added
  7. filtrationAfter 11/2 hours, the mixture is filtered
  8. dry with materialDrying the filtration residue in a vacuum desiccator over P2O5 /KOH (3 hours/80°)

Sources & evidence

ORD record
ord-e91ac0ae43f7441b99fe1c7130d335dd
Source dataset
uspto-grants-1992_12
Patent number
US05175344

Reaction notes

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