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Ozone → Diphenylmethyl alpha-[3-phenoxymethyl-7-oxo-2,6-diaza-4-thiabicyclo[3,2,0]hept-2-en-6-yl]-alpha-(2-chloro-1-hydroxyethylidene)acetate

HRID 971527
Notes
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Reaction equation

HRID 971527 reaction equation
[O:1]([CH2:8][C:9]1[S:15][CH:14]2[CH:11]([C:12](=[O:37])[N:13]2[CH:16]([C:33](=C)[CH2:34][Cl:35])[C:17]([O:19][CH:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:38]=[O+][O-]>C(Cl)Cl.CO>[O:1]([CH2:8][C:9]1[S:15][CH:14]2[CH:11]([C:12](=[O:37])[N:13]2[C:16](=[C:33]([OH:38])[CH2:34][Cl:35])[C:17]([O:19][CH:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[O:18])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 24823OzoneHCID 20464414Diphenylmethyl alpha-[3-phenoxymethyl-7-oxo-2,6-diaza-4-thiabicyclo[3,2,0]hept-2-en-6-yl]-alpha-(1-chloro-2-propen-2-yl)acetate

Product 1

HCID 70504488Diphenylmethyl alpha-[3-phenoxymethyl-7-oxo-2,6-diaza-4-thiabicyclo[3,2,0]hept-2-en-6-yl]-alpha-(2-chloro-1-hydroxyethylidene)acetate

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent
HCID 6344
Dichloromethane
Solvent

Procedure

To a dry ice acetone cooled solution of diphenylmethyl α-[3-phenoxymethyl-7-oxo-2,6-diaza-4-thiabicyclo[3,2,0]hept-2-en-6-yl]-α-(1-chloro-2-propen-2-yl)acetate (160 mg) in a mixture of methylene chloride (3.2 ml) and methanol (0.3 ml) is introduced ozone until the reaction mixture shows blue color. Then excess ozone is purged with oxygen, mixed with an aqueous solution of 95% sodium hydrogen sulfite (100 mg), warmed to room temperature to decompose the ozonide. After 1.5 hours, the solution is washed with 5% sodium hydrogen carbonate and water, dried, and concentrated to remove methylene chloride. The resultant oil (132 mg) is purified over thin-layer chromatographic plate (Merck 60F-254) using a mixture of benzene and ethyl acetate (1:1) as developing solvent to give diphenylmethyl α-[3-phenoxymethyl-7-oxo-2,6-diaza-4-thiabicyclo[3,2,0]-hept-2-en-6-yl]-α-(2-chloro-1-hydroxyethylidene)acetate (44 mg) as glass.

Workup

  1. customThen excess ozone is purged with oxygen
  2. additionmixed with an aqueous solution of 95% sodium hydrogen sulfite (100 mg)
  3. washthe solution is washed with 5% sodium hydrogen carbonate and water
  4. customdried
  5. concentrationconcentrated
  6. customto remove methylene chloride
  7. customThe resultant oil (132 mg) is purified over thin-layer chromatographic plate (Merck 60F-254)
  8. additiona mixture of benzene and ethyl acetate (1:1)

Sources & evidence

ORD record
ord-155d3c82fdca46039eb742ad6226cbb1
Source dataset
uspto-grants-1979_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04160085

Reaction notes

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