Tris(furan-2-yl)phosphane → [3-(4'-{(5S)-5-[(Acetylamino)methyl]-2-oxo-1,3-oxazolidin-3-yl}-1,1'-biphenyl-4-yl)-4,5-dihydroisoxazol-5-yl]methyl di-tert-butyl phosphate

HRID 747242Notes

Reaction equation

HRID 747242 reaction equation
[P:1]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])([O:3][CH2:4][CH:5]1[O:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][C:13](Br)=[CH:12][CH:11]=2)[CH2:6]1)=[O:2].[O:27]=[C:28]1[N:32]([C:33]2[CH:38]=[CH:37][C:36]([Sn](C)(C)C)=[CH:35][CH:34]=2)[CH2:31][C@H:30]([CH2:43][NH:44][C:45](=[O:47])[CH3:46])[O:29]1.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1>O1CCOCC1>[P:1]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])([O:3][CH2:4][CH:5]1[O:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:36]3[CH:35]=[CH:34][C:33]([N:32]4[CH2:31][C@H:30]([CH2:43][NH:44][C:45](=[O:47])[CH3:46])[O:29][C:28]4=[O:27])=[CH:38][CH:37]=3)=[CH:12][CH:11]=2)[CH2:6]1)=[O:2]

Participants

5

Reactant 3

HCID 521585Tris(furan-2-yl)phosphaneHCID 14987823N-({(5S)-2-Oxo-3-[4-(trimethylstannyl)phenyl]-1,3-oxazolidin-5-yl}methyl)acetamideHCID 68597275[3-(4-Bromophenyl)-4,5-dihydroisoxazol-5-yl]methyl di-tert-butyl phosphate

Product 1

HCID 69693473[3-(4'-{(5S)-5-[(Acetylamino)methyl]-2-oxo-1,3-oxazolidin-3-yl}-1,1'-biphenyl-4-yl)-4,5-dihydroisoxazol-5-yl]methyl di-tert-butyl phosphateYield 36.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

[3-(4-Bromophenyl)-4,5-dihydroisoxazol-5-yl]methyl di-tert-butyl phosphate (0.25 g, 0.55 mmol), N-({(5S)-2-oxo-3-[4-(trimethylstannyl)phenyl]-1,3-oxazolidin-5-yl}methyl)acetamide (0.25 g, 0.66 mmol), tri-2-furylphosphine (0.026 g, 0.11 mmol) and tris(dibenzylideneacetone)palladium (0) (0.05 g, 0.55 mmol) were dissolved in 1,4-dioxane (5 ml) and degassed three times. The mixture was heated to 90° C. and stirred for 5 hr, then stirred at 25° C. for 12 hours. The solution was concentrated in vacuo and purified by silica flash chromatography with 5-10% methanol in dichloromethane as eluent giving 0.12 g of the desired product as a yellowish white foam.

Workup

  1. customdegassed three times
  2. stirringstirred at 25° C. for 12 hours
  3. concentrationThe solution was concentrated in vacuo
  4. custompurified by silica flash chromatography with 5-10% methanol in dichloromethane as eluent

Sources & evidence

ORD record
ord-4e666a44e80a4fd482e5ccd9784bf3cf
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Reaction notes

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