2-Azetidinone, 4-(acetyloxy)-3-ethyl- → 3-Ethyl-4-(4-p-nitrobenzyloxycarbonylaminobutyrylthio)-2-oxoazetidine

HRID 1710248Notes

Reaction equation

HRID 1710248 reaction equation
[N+:1]([C:4]1[CH:20]=[CH:19][C:7]([CH2:8][O:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[S:17])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:21]([CH:23]1[CH:26](OC(=O)C)[NH:25][C:24]1=[O:31])[CH3:22]>[OH-].[Na+].O1CCOCC1>[CH2:21]([CH:23]1[CH:26]([S:17][C:16](=[O:18])[CH2:15][CH2:14][CH2:13][NH:12][C:10]([O:9][CH2:8][C:7]2[CH:19]=[CH:20][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[O:11])[NH:25][C:24]1=[O:31])[CH3:22]

Participants

5

Reactant 2

HCID 117884382-Azetidinone, 4-(acetyloxy)-3-ethyl-HCID 178523350HCID 178523350, compound

Product 1

HCID 230357713-Ethyl-4-(4-p-nitrobenzyloxycarbonylaminobutyrylthio)-2-oxoazetidine

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution, prepared in the cold, of 7.95 g (26.7 mmole) of 4-p-nitrobenzyloxycarbonylaminothiobutyric acid in 26.7 ml of 1N sodium hydroxide solution is added dropwise to a pre-cooled solution of 3.24 g (20 mmole) of 3-ethyl-4-acetoxyazetidin-2-one (racemic cis-trans compound in a ratio of 6:4) in 50 ml of dioxan and the mixture is stirred for 2 hours at room temperature. The reaction mixture is exhaustively extracted with methylene chloride. The combined organic phases are dried over sodium sulphate and 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 with the following physico-chemical properties.

Workup

  1. extractionThe reaction mixture is exhaustively extracted with methylene chloride
  2. dry with materialThe combined organic phases are dried over sodium sulphate
  3. concentrationconcentrated by evaporation in vacuo
  4. customThe residue is chromatographed over silica gel with toluene/ethyl acetate (9:1, 4:1 and 1:1)

Sources & evidence

ORD record
ord-8b25489246264d7796b5b162a3316634
Source dataset
uspto-grants-1990_08
Patent number
US04952690

Reaction notes

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