Triphenylphosphine → HCID 86691240, compound

HRID 2038223Notes

Reaction equation

HRID 2038223 reaction equation
[CH2:1]([O:3][CH2:4][CH:5](CS([O-])(=O)=O)[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)[CH3:2].[N-:20]=[N+]=[N-].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C.C1COCC1.O>[CH2:1]([O:3][CH2:4][CH:5]([NH2:20])[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)[CH3:2]

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 33557Sodium AzideHCID 86691241HCID 86691241, compound

Product 1

HCID 86691240HCID 86691240, compoundYield 52.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Dissolve [1-(ethoxymethyl)-2-(4-fluorophenoxy)ethyl]methanesulfonate (2.3 g, 7.87 mmol) in DMF (3 mL) and add sodium azide (1 g, 15.38 mmol) to the mixture. Stir the mixture at 70° C. for 3 hours. Add Et2O (150 mL) and wash with water (3×10 mL). Separate the phases; dry the organic phase over Na2SO4; filter; and concentrate the filtrate under reduced pressure to give a clear oil. Dissolve the oil in a mixture of THF (50 mL) and H2O (12.5 mL). Add triphenylphosphine (3.0 g, 11.44 mmol) and stir at 30° C. for 2 hours. Purify the reaction mixture via SCX-ion exchange chromatography with 1N NH3/MeOH to provide the product fractions. Concentrate the select fractions under reduced pressure and then purify via flash column chromatography using a gradient of 1% to 10% of MeOH in DCM collecting fractions at wavelength of 214 nm. Concentrate under reduced pressure to give the title compound as a colorless oil (880 mg, 33.5%). MS (m/z): 214 (M+1).

Workup

  1. washAdd Et2O (150 mL) and wash with water (3×10 mL)
  2. customSeparate the phases
  3. dry with materialdry the organic phase over Na2SO4
  4. filtrationfilter
  5. concentrationand concentrate the filtrate under reduced pressure
  6. customto give a clear oil
  7. dissolutionDissolve the oil
  8. customPurify the reaction mixture via SCX-ion exchange chromatography with 1N NH3/MeOH
  9. customto provide the product fractions
  10. concentrationConcentrate the select fractions under reduced pressure
  11. custompurify via flash column chromatography
  12. concentrationConcentrate under reduced pressure

Sources & evidence

ORD record
ord-c6aaab17474c4d27b3c72c99b8153c2f
Source dataset
uspto-grants-2013_11
Patent number
US08575352B2

Reaction notes

Loading…