Pyridine → cis-3-[2-(2-Chloroacetamido-4-thiazolyl)-2-methoxyiminoacetamido]-4-chloroacetoxymethyl-2-oxoazetidine

HRID 621151Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 621151
[Cl:1][CH2:2][C:3]([NH:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:22][O:23][CH3:24])[C:12]([NH:14][C@H:15]2[C@@H:18]([CH2:19][OH:20])[NH:17][C:16]2=[O:21])=[O:13])[N:10]=1)=[O:4].N1C=CC=CC=1.[Cl:31][CH2:32][C:33](Cl)=[O:34]>C(Cl)Cl.CN(C)C=O>[Cl:1][CH2:2][C:3]([NH:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:22][O:23][CH3:24])[C:12]([NH:14][C@H:15]2[C@@H:18]([CH2:19][O:20][C:33](=[O:34])[CH2:32][Cl:31])[NH:17][C:16]2=[O:21])=[O:13])[N:10]=1)=[O:4]

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 86740477cis-3-[2-(2-Chloroacetamido-4-thiazolyl)-2-methoxyiminoacetamido]-4-hydroxymethyl-2-oxoazetidine

Produkt 1

HCID 86741506cis-3-[2-(2-Chloroacetamido-4-thiazolyl)-2-methoxyiminoacetamido]-4-chloroacetoxymethyl-2-oxoazetidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In a mixture of 17 ml of methylene chloride and 6 ml of N,N-dimethylformamide is dissolved 172 mg of cis-3-[2-(2-chloroacetamido-4-thiazolyl)-2-methoxyiminoacetamido]-4-hydroxymethyl-2-oxoazetidine (syn-isomer), followed by addition of 0.2 ml of pyridine. While the mixture is cooled with ice-sodium chloride mixture and stirred, 0.12 ml of chloroacetyl chloride is added dropwise. The mixture is stirred under cooling for 30 minutes and the solvent is distilled off. To the residue are added aqueous sodium chloride and ethyl acetate, and the mixture is shaken well. The organic layer is separated and washed with aqueous sodium chloride and dried over anhydrous sodium sulfate. The solvent is then distilled off and the residue is crystallized from ether. Recrystallization from chloroform-methanol gives colorless crystals of cis-3-[2-(2-chloroacetamido-4-thiazolyl)-2-methoxyiminoacetamido]-4-chloroacetoxymethyl-2-oxoazetidine (syn-isomer), m.p. 225°-227° C. (decomp.).

Aufarbeitung

  1. stirringThe mixture is stirred
  2. temperatureunder cooling for 30 minutes
  3. distillationthe solvent is distilled off
  4. additionTo the residue are added aqueous sodium chloride and ethyl acetate
  5. stirringthe mixture is shaken well
  6. customThe organic layer is separated
  7. washwashed with aqueous sodium chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent is then distilled off
  10. customthe residue is crystallized from ether
  11. customRecrystallization from chloroform-methanol

Quellen und Nachweise

ORD-Eintrag
ord-441d9976b9fc47339170f9181f3545ec
Quelldatensatz
uspto-grants-1989_04
Patentnummer
US04822788

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