Triphenylphosphine → 3-(2-(N-t-Butoxycarbonylamino)ethoxy)-5-chloro-1,2-benzisoxazole

HRID 1870272Notes

Reaction equation

HRID 1870272 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].[Cl:43][C:44]1[CH:45]=[CH:46][C:47]2[O:51][N:50]=[C:49](O)[C:48]=2[CH:53]=1>O1CCCC1>[C:32]([O:36][C:37]([NH:39][CH2:40][CH2:41][O:42][C:49]1[C:48]2[CH:53]=[C:44]([Cl:43])[CH:45]=[CH:46][C:47]=2[O:51][N:50]=1)=[O:38])([CH3:35])([CH3:34])[CH3:33]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamateHCID 178518984HCID 178518984, compound

Product 1

HCID 154539363-(2-(N-t-Butoxycarbonylamino)ethoxy)-5-chloro-1,2-benzisoxazoleYield 75.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of triphenylphosphine (0.87 g) in tetrahydrofuran (10 ml), was added diethyl azodicarboxylate (0.57 g) dropwise with stirring under ice cooling. The reaction mixture was stirred at the same temperature for 10 minutes. Then, 2-(N-t-butoxycarbonylamino)ethanol (0.48 g) and 5-chloro-3-hydroxy-1,2-benzisoxazole (0.51 g) were added to the reaction mixture successively and 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 with cyclohexane/ethyl acetate (4/1) as an eluent. The title compound (0.70 g) was obtained as colorless crystals by crystallization from isopropylether.

Workup

  1. stirringThe reaction mixture was stirred at the same temperature for 10 minutes
  2. stirringstirred under ice cooling for 10 minutes and 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 (4/1) as an eluent

Sources & evidence

ORD record
ord-feb141ee5c10430b9e0c2c61800d8af4
Source dataset
uspto-grants-2000_08
Patent number
US06096771

Reaction notes

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