Triphenylphosphine → HCID 53957252, compound

HRID 1735946Notes

Reaction equation

HRID 1735946 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH:5](O)[CH2:6][CH2:7][CH2:8][NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.C1(P([N:64]=[N+:65]=[N-:66])(C2C=CC=CC=2)=O)C=CC=CC=1>C1COCC1.C(O)C.ClCCl>[CH2:1]([O:3][C:4](=[O:18])[CH:5]([N:64]=[N+:65]=[N-:66])[CH2:6][CH2:7][CH2:8][NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH3:2]

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 199401P,P-Diphenylphosphinic azideHCID 5462977Diethyl azodicarboxylateHCID 54439806HCID 54439806, compound

Product 1

HCID 53957252HCID 53957252, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Hydroxy-5-(t-butyloxycarbonylamino)pentanoic acid ethyl ester, (11, 26.1 g, 0.1 mol), triphenylphosphine (26.2 g, 0.10 mol), diethylazodicarboxylate (17.4 g, 0.1 mol), and diphenylphosphorylazide (27.5 g, 0.1 mol) is dissolved in THF (500 mL) and heated to reflux and maintained there for 8 hours. The reaction is cooled to room temperature, evaporated to an oil, and the product isolated by column chromatography using dichloromethane:ethanol as eluent.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. temperaturemaintained there for 8 hours
  4. customevaporated to an oil
  5. customthe product isolated by column chromatography

Sources & evidence

ORD record
ord-1460592f270f41c5ae7d3d2847f5801c
Source dataset
uspto-grants-1996_07
Patent number
US05539082

Reaction notes

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