Ethanol → HCID 3035775, compound

HRID 728893Notes

Reaction equation

HRID 728893 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 withina 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 whilecooling 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 mlof 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. concentrationThe whole is then concentrated by evaporation
  2. dissolutionthe residue is dissolved three times in 70 ml of toluene each time
  3. concentrationin each case is concentrated by evaporation again
  4. dissolutionThe residue is dissolved in 42 ml of ethanol
  5. addition42 mlof propylene oxide are added
  6. filtrationAfter 11/2 hours, the mixture is filtered
  7. dry with materialDrying the filtration residue in a vacuum desiccator over P2O5 /KOH (3 hours/80°)

Sources & evidence

ORD record
ord-10ac1bbe72f3421e97d69cf5e4098ac7
Source dataset
uspto-grants-1991_09
Patent number
US05051413

Reaction notes

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