Ozone → 2-[4-(Benzoxazol-2-yldithio)-3-phenoxyacetamido-2-oxoazetidin-1-yl]-3-hydroxy-crotonic acid diphenylmethyl ester

HRID 26098Notes

Reaction equation

HRID 26098 reaction equation
O=[O+][O-].O=O.O=[O+][O-].[C:9]1([CH:15]([O:22][C:23](=[O:55])[CH:24]([N:28]2[CH:31]([S:32][S:33][C:34]3[O:35][C:36]4[CH:42]=[CH:41][CH:40]=[CH:39][C:37]=4[N:38]=3)[CH:30]([NH:43][C:44](=[O:53])[CH2:45][O:46][C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[C:29]2=[O:54])[C:25](=C)[CH3:26])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C1(C)C=CC=CC=1.C(OCC)(=[O:65])C>C(OCC)(=O)C>[C:9]1([CH:15]([O:22][C:23](=[O:55])/[C:24](/[N:28]2[CH:31]([S:32][S:33][C:34]3[O:35][C:36]4[CH:42]=[CH:41][CH:40]=[CH:39][C:37]=4[N:38]=3)[CH:30]([NH:43][C:44](=[O:53])[CH2:45][O:46][C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[C:29]2=[O:54])=[C:25](\[OH:65])/[CH3:26])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 24823OzoneHCID 21584019Toluene ethylacetateHCID 538001472-[4-(Benzoxazol-2-yldithio)-3-phenoxyacetamido-2-oxoazetidin-1-yl]-3-methylene-butyric acid diphenylmethyl esterHCID 131711318Oxygen ozone

Product 1

HCID 867364472-[4-(Benzoxazol-2-yldithio)-3-phenoxyacetamido-2-oxoazetidin-1-yl]-3-hydroxy-crotonic acid diphenylmethyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(aix) Approximately one equivalent of ozone (in the form of an O2 /O3 mixture) is passed into a solution, cooled to -70° C., of 3.35 g of 2-[4-(benzoxazol-2-yldithio)-3-phenoxyacetamido-2-oxoazetidin-1-yl]-3-methylene-butyric acid diphenylmethyl ester in 125 ml of ethyl acetate, until starting material is no longer detectable by thin layer chromatography (silica gel; toluene/ethyl acetate, 3:1). The solution is concentrated by evaporation to about 50 ml in vacuo, mixed with 5 ml of dimethyl sulphide and stirred until the potassium iodide/starch test no longer gives a reaction. The mixture is concentrated by evaporation in vacuo, the residue is dissolved in 150 ml of benzene and the solution is washed with water. The organic phase is dried over sodium sulphate and concentrated by evaporation. The residue is chromatographed on 150 g of acid-washed silica gel, using toluene/ethyl acetate, 4:1. 2-[4-(Benzoxazol-2-yldithio)-3-phenoxyacetamido-2-oxoazetidin-1-yl]-3-hydroxy-crotonic acid diphenylmethyl ester is obtained in the form of a white foam; IR spectrum (methylene chloride): characteristic bands at 5.60, 5.90 and 6.0 μ.

Workup

  1. concentrationThe solution is concentrated by evaporation to about 50 ml in vacuo
  2. additionmixed with 5 ml of dimethyl sulphide
  3. customno longer gives
  4. customa reaction
  5. concentrationThe mixture is concentrated by evaporation in vacuo
  6. dissolutionthe residue is dissolved in 150 ml of benzene
  7. washthe solution is washed with water
  8. dry with materialThe organic phase is dried over sodium sulphate
  9. concentrationconcentrated by evaporation
  10. customThe residue is chromatographed on 150 g of acid-washed silica gel

Sources & evidence

ORD record
ord-3fab32337586442b92eb3c0de3aab9c8
Source dataset
uspto-grants-1979_04
Patent number
US04147864

Reaction notes

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