Triphenylphosphine → HCID 19596650, compound

HRID 612864Notes

Reaction equation

HRID 612864 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[C:32]([O:36][C:37]([NH:39][CH2:40][CH2:41][OH:42])=[O:38])([CH3:35])([CH3:34])[CH3:33].O[C:44]1[CH:48]=[C:47]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=2[O:55][CH3:56])[O:46][N:45]=1>O1CCCC1>[C:32]([O:36][C:37]([NH:39][CH2:40][CH2:41][O:42][C:44]1[CH:48]=[C:47]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=2[O:55][CH3:56])[O:46][N:45]=1)=[O:38])([CH3:35])([CH3:34])[CH3:33]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamateHCID 178489317HCID 178489317, compound

Product 1

HCID 19596650HCID 19596650, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triphenylphosphine (0.45 g) was dissolved in tetrahydrofuran (5 ml), and diethyl azodicarboxylate (0.27 ml) was added dropwise to the solution under ice-cooling with stirring, and the resulting mixture was stirred at the same temperature for 30 minutes. Then, 2-(N-tert-butoxycarbonylamino)ethanol (0.20 g) and 3-hydroxy-5-(2-methoxyphenyl)isoxazole (0.22 g) were added to the reaction mixture, followed by stirring of the resulting mixture under ice-cooling for 10 minutes and at room temperature for 24 hours. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=4/1) to obtain the title compound (0.33 g, 86%) as colorless crystals.

Workup

  1. temperaturecooling
  2. stirringthe resulting mixture was stirred at the same temperature for 30 minutes
  3. stirringby stirring of the resulting mixture under ice-
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-7b3cb0812046434fa7240ed508b9b617
Source dataset
uspto-grants-1999_12
Patent number
US06005116

Reaction notes

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