Triphenylphosphine → HCID 53961240, compound

HRID 2309073Notes

Reaction equation

HRID 2309073 reaction equation
[N+:1]([C:4]1[CH:25]=[CH:24][C:7]([CH2:8][O:9][C:10](=[O:23])[CH:11]([N:13]2[CH:16]([S:17][C:18](=[O:20])[CH3:19])[CH:15]([CH3:21])[C:14]2=[O:22])Cl)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:26]1([P:32]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O1CCOCC1>[N+:1]([C:4]1[CH:25]=[CH:24][C:7]([CH2:8][O:9][C:10](=[O:23])[C:11]([N:13]2[CH:16]([S:17][C:18](=[O:20])[CH3:19])[CH:15]([CH3:21])[C:14]2=[O:22])=[P:32]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 53667554HCID 53667554, compound

Product 1

HCID 53961240HCID 53961240, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The crude 2-(4-acetylthio-3-methyl-2-oxoazetidin-1-yl)-2-chloroacetic acid p-nitrobenzyl ester obtained is dissolved in 12 ml of absolute dioxan, 1 g of poly-Hunig base is added and the mixture is stirred for 30 minutes, then 312 mg of triphenylphosphine are added and the mixture is stirred under nitrogen for 15 hours at 50°. The poly-Hunig base is filtered off, washed with dioxan and the filtrate and washing liquid are together concentrated by evaporation in vacuo. The residue is chromatographed over silica gel with toluene/ethyl acetate and yields a cis-trans mixture of the title compound having the following physico-chemical properties:

Workup

  1. stirringthe mixture is stirred under nitrogen for 15 hours at 50°
  2. filtrationThe poly-Hunig base is filtered off
  3. washwashed with dioxan
  4. washthe filtrate and washing liquid
  5. concentrationare together concentrated by evaporation in vacuo
  6. customThe residue is chromatographed over silica gel with toluene/ethyl acetate
  7. customyields

Sources & evidence

ORD record
ord-205e8ff1b82947ae84fc52f93aa5ec1c
Source dataset
uspto-grants-1987_09
Patent number
US04692442

Reaction notes

Loading…