Triphenylphosphine → 3-(2-(N-tert-butoxycarbonylamino)ethoxy)-5-phenylisoxazole

HRID 612856Notes

Reaction equation

HRID 612856 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[OH:32][C:33]1[CH:37]=[C:36]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[O:35][N:34]=1.[C:44]([O:48][C:49]([NH:51][CH2:52][CH2:53]O)=[O:50])([CH3:47])([CH3:46])[CH3:45]>O1CCCC1>[C:44]([O:48][C:49]([NH:51][CH2:52][CH2:53][O:32][C:33]1[CH:37]=[C:36]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[O:35][N:34]=1)=[O:50])([CH3:47])([CH3:46])[CH3:45]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamateHCID 178515569HCID 178515569, compound

Product 1

HCID 154349603-(2-(N-tert-butoxycarbonylamino)ethoxy)-5-phenylisoxazoleYield 69.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triphenylphosphine (0.87 g) was dissolved in tetrahydrofuran (10 ml), and diethyl azodicarboxylate (0.57 g) was added dropwise to the solution under ice-cooling with stirring, and the mixture was stirred at the same temperature for 10 minutes. 3-Hydroxy-5-phenylisoxazole (0.48 g) and 2-(N-tert-butoxycarbonylamino)ethanol (0.48 g) were added to the reaction mixture, and the resulting mixture was stirred 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: cyclohexane/ethyl acetate=4/1) and was crystallized from isopropyl ether to obtain the title compound (0.63 g, 69%) as colorless crystals.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at the same temperature for 10 minutes
  3. stirringthe resulting mixture was stirred under ice-
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent: cyclohexane/ethyl acetate=4/1)
  6. customwas crystallized from isopropyl ether

Sources & evidence

ORD record
ord-3ddb34e233714ee983aba89a281822f4
Source dataset
uspto-grants-1999_12
Patent number
US06005116

Reaction notes

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