Triphenylphosphine → HCID 15453940, compound

HRID 1870279Notes

Reaction equation

HRID 1870279 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[F:32][C:33]1[CH:34]=[CH:35][C:36]2[O:40][N:39]=[C:38]([OH:41])[C:37]=2[CH:42]=1.[C:43]([O:47][C:48]([NH:50][CH2:51][CH2:52]O)=[O:49])([CH3:46])([CH3:45])[CH3:44]>O1CCCC1>[C:43]([O:47][C:48]([NH:50][CH2:51][CH2:52][O:41][C:38]1[C:37]2[CH:42]=[C:33]([F:32])[CH:34]=[CH:35][C:36]=2[O:40][N:39]=1)=[O:49])([CH3:46])([CH3:45])[CH3:44]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamateHCID 178518988HCID 178518988, compound

Product 1

HCID 15453940HCID 15453940, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of triphenylphosphine (0.87 g) in tetrahydrofuran (20 ml) was added diethyl azodicarboxylate (0.57 g) at 5° C. and the mixture was stirred at the same temperature for 15 minutes. Then 5-fluoro-3-hydroxy-1,2-benzisoxazole (0.46 g) was added and the mixture was stirred at the same temperature for 15 minutes followed by addition of N-t-butoxycarbonyl ethanolamine (0.48 g) and stirring at room temperature for 24 hours. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography with cyclohexane/ethyl acetate (9/1) as an eluent, to give the title compound (0.53 g, 60%) as a colorless powder.

Workup

  1. stirringthe mixture was stirred at the same temperature for 15 minutes
  2. stirringstirring at room temperature for 24 hours
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography with cyclohexane/ethyl acetate (9/1) as an eluent

Sources & evidence

ORD record
ord-415d4c1189e047c39a0c304507c714a8
Source dataset
uspto-grants-2000_08
Patent number
US06096771

Reaction notes

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