Triphenylphosphine → HCID 58446432, compound

HRID 1773767Notes

Reaction equation

HRID 1773767 reaction equation
C([O:9][C@@H:10]1[C@H:17]([O:18]C(=O)C2C=CC=CC=2)[C@@H:16]([CH2:27][O:28]C(=O)C2C=CC=CC=2)[O:15][C@H:11]1[C:12]([OH:14])=O)(=O)C1C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C=C(SSC2N=CC=CC=2)N=CC=1.[CH3:70][O:71][C:72]1[CH:79]=[CH:78][C:75]([NH:76][CH3:77])=[CH:74][CH:73]=1>C1COCC1>[OH:9][C@@H:10]1[C@H:17]([OH:18])[C@@H:16]([CH2:27][OH:28])[O:15][CH:11]1[C:12]([N:76]([C:75]1[CH:78]=[CH:79][C:72]([O:71][CH3:70])=[CH:73][CH:74]=1)[CH3:77])=[O:14]

Participants

6

Reactant 4

HCID 11776Triphenylphosphine2×HCID 22250N-Methyl-4-anisidineHCID 650932,2'-Dipyridyl disulfideHCID 10435678D-Allonic acid, 2,5-anhydro-, 3,4,6-tribenzoate

Product 1

HCID 58446432HCID 58446432, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3,4,6-Tri-O-benzoyl-2,5-anhydro-D-allonic acid (2 g, 4 mmol) was dissolved in anhydrous THF (40 mL) under argon, and triphenylphosphine (2.1 g, 8 mmol) was added to the mixture. The resultant mixture was stirred until the triphenylphosphine was completely dissolved and subsequently 2,2′-dipyridyldisulfide (1.8 g, 8 mmol) was added. The mixture was stirred at room temperature for 2 hours, after which the 4-methoxy-N-methyl-aniline (0.768 g, 5.6 mmol) was added and stirring was continued at room temperature for 16 hours. The solvent was evaporated to dryness, the residue was dissolved in chloroform (150 mL) and washed twice with 0.1 M NaOH solution (100 mL), twice with 0.2 M HCl solution (100 mL), once with saturated NaHCO3 solution (100 mL) and dried (Na2SO4). The solvent was evaporated to dryness and the residue was dissolved in 7M ammonia solution in methanol (250 ml) and stirred for 16 hours at room temperature and then evaporated to dryness. The residue was dissolved in chloroform and applied to a column of silica gel. Elution with a mixture of chloroform methanol (3:1) and evaporation of the appropriate fractions yielded the title compound as an off-white solid (0.77 g, 2.6 mmol, 65%): MS (ES) m/z 320 [M+Na]+.

Workup

  1. dissolutionwas completely dissolved
  2. stirringstirring
  3. waitwas continued at room temperature for 16 hours
  4. customThe solvent was evaporated to dryness
  5. dissolutionthe residue was dissolved in chloroform (150 mL)
  6. washwashed twice with 0.1 M NaOH solution (100 mL), twice with 0.2 M HCl solution (100 mL), once with saturated NaHCO3 solution (100 mL)
  7. dry with materialdried (Na2SO4)
  8. customThe solvent was evaporated to dryness
  9. dissolutionthe residue was dissolved in 7M ammonia solution in methanol (250 ml)
  10. stirringstirred for 16 hours at room temperature
  11. customevaporated to dryness
  12. dissolutionThe residue was dissolved in chloroform
  13. washElution
  14. additionwith a mixture of chloroform methanol (3:1) and evaporation of the appropriate fractions

Sources & evidence

ORD record
ord-39c53be4beb943aa9b66527677391f58
Source dataset
uspto-grants-2016_02
Patent number
US09255121B2

Reaction notes

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