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Ethyl Acetate → 2-Benzhydryloxycarbonyl-7-(3,4-dichlorophenylthio)-acetamido-3-(2-nicotinoylamino-thiazol-5-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene

HRID 2413447
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2413447
Cl[C:2]1[CH:3]=[C:4]([CH2:9][C:10](Cl)=S)[CH:5]=[CH:6][C:7]=1Cl.[C:13]([Cl:18])(=O)[C:14]([Cl:16])=O.N[CH:20]1[C:27](=[O:28])[N:26]2[CH:21]1[S:22][CH2:23][C:24]([C:45]1[S:49][C:48]([NH:50][C:51](=[O:58])[C:52]3[CH:57]=[CH:56][CH:55]=[N:54][CH:53]=3)=[N:47][CH:46]=1)=[C:25]2C(OC(C1C=CC=CC=1)C1C=CC=CC=1)=O.[C:59]([O:62]CC)(=[O:61])[CH3:60]>C(OCC)C.CN(C)C(=O)C>[CH:9]([O:62][C:59]([CH2:60][C:27]([NH:26][C:25]1[N:26]2[CH:21]([S:22][CH2:23][C:24]=1[C:45]1[S:49][C:48]([NH:50][C:51](=[O:58])[C:52]3[CH:57]=[CH:56][CH:55]=[N:54][CH:53]=3)=[N:47][CH:46]=1)[CH:20]([S:49][C:45]1[CH:24]=[CH:23][C:14]([Cl:16])=[C:13]([Cl:18])[CH:46]=1)[C:27]2=[O:28])=[O:28])=[O:61])([C:4]1[CH:3]=[CH:2][CH:7]=[CH:6][CH:5]=1)[C:10]1[CH:55]=[CH:56][CH:57]=[CH:52][CH:51]=1
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Komponenten

7

Edukt 4

HCID 8857Ethyl Acetate2×HCID 65578Oxalyl chlorideHCID 202763043,4-Dichlorophenylthioacetyl chlorideHCID 204304287-Amino-2-benzhydryloxycarbonyl-3-(2-nicotinoylamino-thiazol-5-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene

Produkt 1

HCID 86739904
2-Benzhydryloxycarbonyl-7-(3,4-dichlorophenylthio)-acetamido-3-(2-nicotinoylamino-thiazol-5-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

A solution of 3,4-dichlorophenylthioacetyl chloride (prepared by the action of oxalyl chloride (8.4 cc) on the corresponding acid (3.99 g) in ethyl ether (48 cc), and replacement of the solvent) in ethyl acetate (20 cc) is added, in 10 minutes, to a solution of 7-amino-2-benzhydryloxycarbonyl-3-(2-nicotinoylamino-thiazol-5-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (6.43 g) in N,N-dimethylacetamide (25 cc) at 0° C. After 1 hour at 0° C. followed by 40 minutes at a temperature of between 0 ° and 20° C., the reaction mixture is poured into ethyl acetate (250 cc) and this mixture is washed with distilled water (3×100 cc) and then with a saturated sodium chloride solution (100 cc). The organic phase is dried and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residue is filtered on a column of silica (0.02-0.5 mm) (40 g), elution being carried out with a mixture (2 liters) of methylene chloride and methanol (95:5 by volume). The residue obtained after concentrating to dryness under reduced pressure (30 mm Hg; 4 kPa) at 30° C. is crystallised from methylene chloride (20 cc) to give 2-benzhydryloxycarbonyl-7-(3,4-dichlorophenylthio)-acetamido-3-(2-nicotinoylamino-thiazol-5-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (2.9 g) in the form of a pale yellow crystalline solid.

Aufarbeitung

  1. washthis mixture is washed with distilled water (3×100 cc)
  2. customThe organic phase is dried
  3. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  4. filtrationThe residue is filtered on a column of silica (0.02-0.5 mm) (40 g), elution
  5. customThe residue obtained
  6. concentrationafter concentrating to dryness under reduced pressure (30 mm Hg; 4 kPa) at 30° C.
  7. customis crystallised from methylene chloride (20 cc)

Quellen und Nachweise

ORD-Eintrag
ord-33cef257d50f4dd1bcb4a8e379714dc7
Quelldatensatz
uspto-grants-1985_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04496560

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