Water → HCID 69637519, compound

HRID 352993Notes

Reaction equation

HRID 352993 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:20]([CH2:23][C@@H:24]([C@H:26]1[O:30][C:29](=[O:31])[C:28]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[C:27]1[O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[OH:25])=[N+]=[N-].O>C1COCC1>[NH2:20][CH2:23][C@@H:24]([C@H:26]1[O:30][C:29](=[O:31])[C:28]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[C:27]1[O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[OH:25]

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 86588996HCID 86588996, compound

Product 1

HCID 69637519HCID 69637519, compoundYield 21.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triphenylphosphine (600 mg, 2.4 mmol) was added to a stirred solution of (R)-5-(2-azido-(S)-1-hydroxyethyl)-3,4-dibenzyloxy-5H-furan-2-one (5) (750 mg, 2 mmol) in THF (10 ml) and after a few minutes gas was evolved. The stirring was continued until the effervescence had ceased (typically 2-3 h) and water (2 ml) was then added and the mixture stirred for a further 1 hour. The THF was removed under reduced pressure and the residue partitioned between dichloromethane (25 ml) and water (25 ml). The organic phase was separated, dried (MgSO4), filtered and any volatile components evaporated under reduced pressure (45° C. at 8 mm/Hg) to leave a viscous orange residue which was purified by chromatography on silica. Initial elution with a dichloromethane:methanol (19:1) mixture removed the less polar by-products and the product was then isolated by elution with a dichloromethane:methanol (3:1) mixture as a pale yellow oil (150 mg; 21%) (Rf0.25).

Workup

  1. customtypically 2-3 h
  2. additionwas then added
  3. customThe THF was removed under reduced pressure
  4. customthe residue partitioned between dichloromethane (25 ml) and water (25 ml)
  5. customThe organic phase was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customany volatile components evaporated under reduced pressure (45° C. at 8 mm/Hg)
  9. customto leave a viscous orange residue which
  10. customwas purified by chromatography on silica
  11. washInitial elution with a dichloromethane:methanol (19:1) mixture
  12. customremoved the less polar by-products

Sources & evidence

ORD record
ord-b713a1b0933840e1b534c393ddcd3284
Source dataset
uspto-grants-2004_06
Patent number
US06749832B2

Reaction notes

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