Triphenylphosphine → 3-[2-Tert-butoxycarbonylamino-3-(3-benzenesulfonyloxy-5-isoxazolyl)propoxy]-5-chloro-1,2-benzoisoxazole

HRID 1901645Notes

Reaction equation

HRID 1901645 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:12][C:13]1[O:17][N:16]=[C:15]([O:18][S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH:14]=1)[CH2:10][OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:28][C:29]1[CH:30]=[CH:31][C:32]2[O:36][N:35]=[C:34](O)[C:33]=2[CH:38]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:12][C:13]1[O:17][N:16]=[C:15]([O:18][S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:20])=[O:21])[CH:14]=1)[CH2:10][O:11][C:34]1[C:33]2[CH:38]=[C:29]([Cl:28])[CH:30]=[CH:31][C:32]=2[O:36][N:35]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 233684952-Tert-butoxycarbonylamino-3-(3-benzenesulfonyloxyisoxazol-5-yl)-1-propanolHCID 178518984HCID 178518984, compound

Product 1

HCID 233684903-[2-Tert-butoxycarbonylamino-3-(3-benzenesulfonyloxy-5-isoxazolyl)propoxy]-5-chloro-1,2-benzoisoxazoleYield 73.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.5 g of 2-tert-butoxycarbonylamino-3-(3-benzenesulfonyloxyisoxazol-5-yl)-1-propanol in 5 ml of tetrahydrofuran are added 0.21 g of 5-chloro-3-hydroxy-1,2-benzoisoxazole, 0.43 g of triphenylphosphine and 0.28 g of diethyl azodicarboxylate with ice-cooling, and they are subjected to reaction at room temperature for 24 hours. Thereafter, the solvent is removed by distillation under reduced pressure. The residue obtained is purified by a column chromatography [eluant:n-hexane:ethyl acetate=4:1], to obtain 0.5 g of oily 3-[2-tert-butoxycarbonylamino-3-(3-benzenesulfonyloxy-5-isoxazolyl)propoxy]-5-chloro-1,2-benzoisoxazole.

Workup

  1. temperaturecooling
  2. customthey are subjected to reaction at room temperature for 24 hours
  3. customThereafter, the solvent is removed by distillation under reduced pressure
  4. customThe residue obtained
  5. customis purified by a column chromatography [eluant:n-hexane:ethyl acetate=4:1]

Sources & evidence

ORD record
ord-05123b0f23e243eabd95df5d2c350898
Source dataset
uspto-grants-1996_11
Patent number
US05578627

Reaction notes

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