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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 325477
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 325477
[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
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Komponenten

5

Edukt 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

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel
HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

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-2en-6-yl]-α-(2-chloro-1-hydroxyethylidene)acetate (44 mg) as glass.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-13b827f286244310b3a21a4f758a6fc5
Quelldatensatz
uspto-grants-1984_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04440683

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