1,2-Dichloroethane → HCID 70466378, compound

HRID 904994Notes

Reaction equation

HRID 904994 reaction equation
[C:1]1([C:7]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:8]2[C@@H:11]([S:12]([CH3:15])(=[O:14])=[O:13])[NH:10][C:9]2=[O:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:29]1(S([O-])=O)[CH:34]=[CH:33]C=[CH:31][CH:30]=1.[Na+].ClCCCl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:23]1([C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C@H:8]2[CH:11]([S:12]([C:15]3[CH:33]=[CH:34][CH:29]=[CH:30][CH:31]=3)(=[O:14])=[O:13])[NH:10][C:9]2=[O:16])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 2723840Benzenesulfinic acid, sodium saltHCID 53694746HCID 53694746, compound

Product 1

HCID 70466378HCID 70466378, compoundYield 72.8%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

A mixture of 30 g of (3R-cis)-3-triphenylmethyl-4-methylsulfonyl-2-azetidinone, 40 g of sodium benzenesulfinate, 25 g of tetra-n-butylammonium bromide, 400 ml of 1,2-dichloroethane, and 100 ml of water were refluxed under nitrogen for 30 minutes. The dichloroethane was removed in vacuo and the residue was extracted with 700 ml of ethyl acetate. The extract was washed with saturated aqueous sodium bicarbonate solution, then water, then saturated aqueous sodium chloride solution. The extract was dried over sodium sulfate and evaporated. The residue was chromatographed on a 50×280 mm silica gel column eluted with 1000 ml 1:4 ethyl acetate:hexane, then 1000 ml 1:1 ethyl acetate:hexane. (3R)-3-triphenylmethyl-4-phenylsulfonyl-2-azetidinone (25.3 g) was obtained as a mixture of cis and trans isomers.

Workup

  1. temperaturewere refluxed under nitrogen for 30 minutes
  2. customThe dichloroethane was removed in vacuo
  3. extractionthe residue was extracted with 700 ml of ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium bicarbonate solution
  5. dry with materialThe extract was dried over sodium sulfate
  6. customevaporated
  7. customThe residue was chromatographed on a 50×280 mm silica gel column
  8. washeluted with 1000 ml 1:4 ethyl acetate

Sources & evidence

ORD record
ord-5b2f91555bf04cb08578cc3779def4a5
Source dataset
uspto-grants-1983_12
Patent number
US04421686

Reaction notes

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