Triphenylphosphine → HCID 53957252, compound

HRID 965319Notes

Reaction equation

HRID 965319 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-64ab020af22546b79b573c99df703b8d
Source dataset
uspto-grants-1998_06
Patent number
US05773571

Reaction notes

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