Triphenylphosphine → HCID 56629358, compound

HRID 1710242Notes

Reaction equation

HRID 1710242 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:20]([C:23]1[CH:54]=[CH:53][C:26]([CH2:27][O:28][C:29](=[O:52])[CH:30]([N:32]2[C@H:35]([S:36][C:37](=[O:39])[CH3:38])[C@@H:34]([O:40][C:41](=[O:50])[CH2:42][O:43][C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[C:33]2=[O:51])Cl)=[CH:25][CH:24]=1)([O-:22])=[O:21]>O1CCOCC1>[N+:20]([C:23]1[CH:24]=[CH:25][C:26]([CH2:27][O:28][C:29](=[O:52])[C:30]([N:32]2[C@H:35]([S:36][C:37](=[O:39])[CH3:38])[C@@H:34]([O:40][C:41](=[O:50])[CH2:42][O:43][C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=3)[C:33]2=[O:51])=[P:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:53][CH:54]=1)([O-:22])=[O:21]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 86744190HCID 86744190, compound

Product 1

HCID 56629358HCID 56629358, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

786 mg of triphenylphosphine and 3 g of poly-Hunig base are added to a solution of 960 mg of 2-[(3S,4R)-4-acetylthio-3-phenoxyacetoxy-2-oxoazetidin-1-yl]-2-chloroacetic acid p-nitrobenzyl ester in 40 ml of dioxan and the mixture is stirred overnight at 50° under nitrogen. The poly-Hunig base is removed by filtration and the filtrate is concentrated by evaporation in vacuo. The residue is chromatographed over silica gel with toluene/ethyl acetate (9:1, 4:1 and 1:1) and yields the title compound. IR spectrum (in methylene chloride): characteristic absorption bands at 5.7, 5.9, 6.17, 6.55 and 7.45 μ.

Workup

  1. customThe poly-Hunig base is removed by filtration
  2. concentrationthe filtrate is concentrated by evaporation in vacuo
  3. customThe residue is chromatographed over silica gel with toluene/ethyl acetate (9:1, 4:1 and 1:1)

Sources & evidence

ORD record
ord-f3e9596df6c7453e998fdfb21c53f5de
Source dataset
uspto-grants-1990_08
Patent number
US04952690

Reaction notes

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