Phenylacetyl chloride → HCID 70390633, Verbindung

HRID 2231566Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2231566
C(N(CC)CC)C.[CH3:8][O:9][C:10]([C@H:12]1[N:15]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=2[O:25][CH3:26])[C:14](=[O:27])[C@H:13]1[NH2:28])=[O:11].[C:29]1([CH2:35][C:36](Cl)=[O:37])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(Cl)Cl>[CH3:8][O:9][C:10]([C@H:12]1[N:15]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=2[O:25][CH3:26])[C:14](=[O:27])[C@H:13]1[NH:28][C:36](=[O:37])[CH2:35][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:11]

Komponenten

5

Edukt 3

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 14095500HCID 14095500, Verbindung

Produkt 1

HCID 70390633HCID 70390633, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Under ice-cooling and stirring, 2.10 ml of triethylamine is added to a solution of 2.94 g of cis-3-amino-1-(2,4-dimethoxybenzyl)-2-oxoazetidine-4-carboxylic acid methyl ester in 40 ml of methylene chloride, and a solution of 2.31 g of phenylacetyl chloride in 15 ml of methylene chloride is then added dropwise over 1 hour. The stirring is continued for another one hour under ice-cooling, and the reaction mixture is then washed successively with dilute hydrochloric acid, 5% aqueous sodium hydrogen carbonate and an aqueous sodium chloride solution, and dried over magnesium sulfate, and the solvent is distilled off in vacuo. Ether is added to the residue and the precipitated crystals are collected by filtration to give cis-1-(2,4-dimethoxybenzyl)-3-phenylacetamido-2-oxoazetidine-4-carboxylic acid methyl ester, m.p. 124°-126° C.

Aufarbeitung

  1. temperatureUnder ice-cooling
  2. temperaturecooling
  3. washthe reaction mixture is then washed successively with dilute hydrochloric acid, 5% aqueous sodium hydrogen carbonate
  4. dry with materialan aqueous sodium chloride solution, and dried over magnesium sulfate
  5. distillationthe solvent is distilled off in vacuo
  6. additionEther is added to the residue
  7. filtrationthe precipitated crystals are collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-5d2a1fdde9664f01b77a5855f6f334b6
Quelldatensatz
uspto-grants-1988_11
Patentnummer
US04782147

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