Ozone → 2-[4-(Benzthiazol-2-yldithio)-3-phenoxyacetamido-2-oxo-azetidin-1-yl]-3-hydroxy-crotonic acid diphenylmethyl ester

HRID 26100Notes

Reaction equation

HRID 26100 reaction equation
[O:1]=[O+][O-].[C:4]1([CH:10]([O:17][C:18](=[O:50])[CH:19]([N:23]2[CH:26]([S:27][S:28][C:29]3[S:30][C:31]4[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=4[N:33]=3)[CH:25]([NH:38][C:39](=[O:48])[CH2:40][O:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C:24]2=[O:49])[C:20](=C)[CH3:21])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(OCC)(=O)C>[C:11]1([CH:10]([O:17][C:18](=[O:50])/[C:19](/[N:23]2[CH:26]([S:27][S:28][C:29]3[S:30][C:31]4[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=4[N:33]=3)[CH:25]([NH:38][C:39](=[O:48])[CH2:40][O:41][C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)[C:24]2=[O:49])=[C:20](\[OH:1])/[CH3:21])[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 24823OzoneHCID 99988benzhydryl 2-(benzothiazol-2-yldithio)-alpha-(isopropenyl)-4-oxo-3-[(phenoxyacetyl)amino]azetidine-1-acetate

Product 1

HCID 867364482-[4-(Benzthiazol-2-yldithio)-3-phenoxyacetamido-2-oxo-azetidin-1-yl]-3-hydroxy-crotonic acid diphenylmethyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1 equivalent of ozone (diluted with oxygen) is passed into a solution, cooled to -70° C., of 681 mg (1.0 mM) of 2-[4-(benzthiazol-2-yldithio)-3-phenoxyacetamido-2-oxoazetidin-1-yl]-3-methylene-butyric acid diphenylmethyl ester in 30 ml of ethyl acetate. The reaction solution is allowed to warm up, concentrated to 10 ml in vacuo, mixed with 1.0 ml of dimethyl sulphide and stirred for 15 hours at room temperature. Solvent and excess reagent are removed in vacuo and the residue is chromatographed on 30 g of acid-washed silica gel, using toluene/ethyl acetate, 4:1 (15 ml fractions). 2-[4-(Benzthiazol-2-yldithio)-3-phenoxyacetamido-2-oxoazetidin- 1-yl]-3-hydroxy-crotonic acid diphenylmethyl ester is obtained as a solid amorphous substance. [α]D = 130° ± 1° (CHCl3 ; c= 0.8) IR spectrum (CH2Cl2): 2.95, 5.60, 5.92, 6.04 and 8.10 μ.

Workup

  1. temperatureto warm up
  2. concentrationconcentrated to 10 ml in vacuo
  3. additionmixed with 1.0 ml of dimethyl sulphide
  4. customSolvent and excess reagent are removed in vacuo
  5. customthe residue is chromatographed on 30 g of acid-washed silica gel

Sources & evidence

ORD record
ord-de7742317b1f4ef88a241d188100bdcc
Source dataset
uspto-grants-1979_04
Patent number
US04147864

Reaction notes

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