Triphenylphosphine → HCID 54214675, compound

HRID 1004331Notes

Reaction equation

HRID 1004331 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:10][C:9]([CH2:11][CH:12]([CH:20](O)[CH3:21])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:8][CH:7]=1)=[O:5])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:42](C(OCC)=O)=NC(OCC)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>O1CCCC1>[NH2:42][CH:20]([CH3:21])[CH:12]([CH2:11][C:9]1[O:10][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:7][CH:8]=1)[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 199401P,P-Diphenylphosphinic azideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 86755321HCID 86755321, compound

Product 1

HCID 54214675HCID 54214675, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 1.65 g of tert-butyl (2RS,3SR)-2-{5-(ethoxycarbonyl)-2-furylmethyl}-3-hydroxybutanoate in 40 ml of tetrahydrofuran, 2.32 g of triphenylphosphine, 1.40 ml of diethyl azodicarboxylate and 2.43 g of diphenylphosphoryl azide were added successively under cooling with ice under stirring, and the resulting reaction solution was stirred at room temperature for 18 hours. The reaction solution was evaporated to dryness under reduced pressure, and the residue was purified by silica gel column chromatography [hexane/ethyl acetate=12/1→3/1]. The resulting azide was refluxed together with 2.33 g of triphenylphosphine in 33 ml of 10% hydrous tetrahydrofuran under heating for 3 hours. The reaction solution was cooled to room temperature, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography [hexane/ethyl acetate=1/1→ethyl acetate/methanol=10/1] to give 686 mg of the title compound as a pale yellow oily substance.

Workup

  1. temperatureunder cooling with ice
  2. customthe resulting reaction solution
  3. stirringwas stirred at room temperature for 18 hours
  4. customThe reaction solution was evaporated to dryness under reduced pressure
  5. customthe residue was purified by silica gel column chromatography [hexane/ethyl acetate=12/1→3/1]
  6. temperatureThe resulting azide was refluxed together with 2.33 g of triphenylphosphine in 33 ml of 10% hydrous tetrahydrofuran
  7. temperatureunder heating for 3 hours
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified by silica gel column chromatography [hexane/ethyl acetate=1/1→ethyl acetate/methanol=10/1]

Sources & evidence

ORD record
ord-2cf7f41c26d44e248712239e0d811dd2
Source dataset
uspto-grants-2000_04
Patent number
US06048894

Reaction notes

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