Triphenylphosphine → 2-[(4R)-4-Acetylthio-2-oxoazetidin-1-yl]-2-triphenylphosphoranylideneacetic acid p-nitrobenzyl ester

HRID 1248427Notes

Reaction equation

HRID 1248427 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:43]=[CH:42][C:26]([CH2:27][O:28][C:29](=[O:41])[CH:30]([N:32]2[C@H:35]([S:36][C:37](=[O:39])[CH3:38])[CH2:34][C:33]2=[O:40])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:41])[C:30]([N:32]2[C@H:35]([S:36][C:37](=[O:39])[CH3:38])[CH2:34][C:33]2=[O:40])=[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:42][CH:43]=1)([O-:22])=[O:21]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 539515252-[(4R)-4-acetylthio-2-oxoazetidin-1-yl]-2-chloroacetic acid p-nitrobenzyl ester

Product 1

HCID 185979042-[(4R)-4-Acetylthio-2-oxoazetidin-1-yl]-2-triphenylphosphoranylideneacetic acid p-nitrobenzyl ester

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3.144 g (~1.5 equivalents) of triphenylphosphine and 12 g of poly-Hunig base are added to a solution of 3.1 g of 2-[(4R)-4-acetylthio-2-oxoazetidin-1-yl]-2-chloroacetic acid p-nitrobenzyl ester in 120 ml of dioxan and the mixture is stirred for 17 hours at 50° under nitrogen. The poly-Hunig base is filtered off, washed with dioxan and the filtrate concentrated in vacuo. The residue is chromatographed twice over silica gel with toluene and toluene/ethyl acetate (4:1 and 3:2) and yields the title compound.

Workup

  1. filtrationThe poly-Hunig base is filtered off
  2. washwashed with dioxan
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe residue is chromatographed twice over silica gel with toluene and toluene/ethyl acetate (4:1 and 3:2)

Sources & evidence

ORD record
ord-bc01107c23dc4e8daea85f460cf78494
Source dataset
uspto-grants-1985_06
Patent number
US04524028

Reaction notes

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