Water → cis-4-Acetoxymethyl-3-[2-(2-chloroacetamido-4-thiazolyl)-2-methoxyiminoacetamido]-2-oxoazetidine

HRID 2231564Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2231564
[C:1]([O:4][CH2:5][C@H:6]1[NH:9][C:8](=[O:10])[C@H:7]1[NH2:11])(=[O:3])[CH3:2].C(=O)([O-])O.[Na+].[Cl:17][CH2:18][C:19]([NH:21][C:22]1[S:23][CH:24]=[C:25]([C:27](=[N:31][O:32][CH3:33])[C:28](Cl)=[O:29])[N:26]=1)=[O:20].O>O1CCCC1>[C:1]([O:4][CH2:5][C@H:6]1[NH:9][C:8](=[O:10])[C@H:7]1[NH:11][C:28](=[O:29])[C:27]([C:25]1[N:26]=[C:22]([NH:21][C:19](=[O:20])[CH2:18][Cl:17])[S:23][CH:24]=1)=[N:31][O:32][CH3:33])(=[O:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 538001502-(2-Chloroacetamido-4-thiazolyl)-2-methoxyiminoacetyl chlorideHCID 70390316cis-4-Acetoxymethyl-3-amino-2-oxoazetidine

Produkt 1

HCID 86740461cis-4-Acetoxymethyl-3-[2-(2-chloroacetamido-4-thiazolyl)-2-methoxyiminoacetamido]-2-oxoazetidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Under ice-cooling and stirring, 12 ml of an aqueous solution containing 632 mg of cis-4-acetoxymethyl-3-amino-2-oxoazetidine and 1.122 g of sodium hydrogen carbonate is added to a suspension of 2.36 of 2-(2-chloroacetamido-4-thiazolyl)-2-methoxyiminoacetyl chloride (syn-isomer) in 20 ml of tetrahydrofuran. The mixture is stirred for 2 hours at room temperature and the solvent is then distilled off in vacuo to leave the residue, which solidifies. Water is added to the solidified residue, followed by filtration. The collected crystals are washed successively with an aqueous sodium hydrogen carbonate solution, water and ether and dried to give cis-4-acetoxymethyl-3-[2-(2-chloroacetamido-4-thiazolyl)-2-methoxyiminoacetamido]-2-oxoazetidine (syn-isomer), m.p. 180°-190° C. (dec.).

Aufarbeitung

  1. temperatureUnder ice-cooling
  2. stirringThe mixture is stirred for 2 hours at room temperature
  3. distillationthe solvent is then distilled off in vacuo
  4. customto leave the residue, which
  5. filtrationfollowed by filtration
  6. washThe collected crystals are washed successively with an aqueous sodium hydrogen carbonate solution, water and ether
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-19c0ace6bf31437eb4c7260f3466f237
Quelldatensatz
uspto-grants-1988_11
Patentnummer
US04782147

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