Tetrahydrofuran → HCID 67431241, compound

HRID 1662793Notes

Reaction equation

HRID 1662793 reaction equation
[Br-].OCCC[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[Cl:35][C:36]1[CH:37]=[C:38]2[C:42](=[CH:43][CH:44]=1)[N:41]([S:45]([C:48]1[CH:53]=[CH:52][C:51]([O:54][CH3:55])=[CH:50][C:49]=1[O:56][C:57]([F:60])([F:59])[F:58])(=[O:47])=[O:46])[C:40](=[O:61])[C:39]2([N:73]1[CH2:82][C@H:81]([OH:83])[CH2:80][C@H:74]1[C:75]([N:77]([CH3:79])[CH3:78])=[O:76])[C:62]1[CH:67]=[C:66]([CH2:68]C=O)[CH:65]=[CH:64][C:63]=1[O:71][CH3:72].[NH4+].[Cl-].[CH2:86]1[CH2:90][O:89][CH2:88][CH2:87]1>>[Cl:35][C:36]1[CH:37]=[C:38]2[C:42](=[CH:43][CH:44]=1)[N:41]([S:45]([C:48]1[CH:53]=[CH:52][C:51]([O:54][CH3:55])=[CH:50][C:49]=1[O:56][C:57]([F:60])([F:58])[F:59])(=[O:47])=[O:46])[C:40](=[O:61])[C:39]2([N:73]1[CH2:82][C@H:81]([OH:83])[CH2:80][C@H:74]1[C:75]([N:77]([CH3:79])[CH3:78])=[O:76])[C:62]1[CH:67]=[C:66]([CH2:68][CH:90]=[CH:86][CH2:87][CH2:88][OH:89])[CH:65]=[CH:64][C:63]=1[O:71][CH3:72]

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran3×HCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 11025793(3-Hydroxypropyl)triphenylphosphonium bromideHCID 59867806HCID 59867806, compound

Product 1

HCID 67431241HCID 67431241, compound

Procedure

Under nitrogen atmosphere, to a suspension of 497 mg of (3-hydroxy propyl)(triphenyl) phosphonium bromide in THF (5 ml) was added dropwise a solution of 1 mol/L lithium bis-(trimethylsilyl) amide in THF (1.43 ml) under ice cooling. After stirring at room temperature for one hour, the solution was cooled by ice, 300 mg of compound obtained in Example 219 in THF (5 ml) was added to a solution and the reaction mixture was stirred at room temperature for one hour. A saturated aqueous solution of NH4Cl was added to the solution and the resulting mixture was extracted with EtOAc; the organic layer was washed with saturated brine and dried over Na2SO4, then, the drying agent was separated by filtration and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (silicagel 60N; mobile phase: CHCl3/MeOH=20/1 to 10/1; v/v) to obtain 206 mg of the title compound.

Workup

  1. additionwas added to a solution
  2. stirringthe reaction mixture was stirred at room temperature for one hour
  3. extractionthe resulting mixture was extracted with EtOAc
  4. washthe organic layer was washed with saturated brine
  5. dry with materialdried over Na2SO4
  6. customthe drying agent was separated by filtration
  7. customthe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified by column chromatography (silicagel 60N; mobile phase: CHCl3/MeOH=20/1 to 10/1; v/v)

Sources & evidence

ORD record
ord-237cc550a6a64deb8b9c4db0014bef8e
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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