Potassium Carbonate → cis-3-Phenoxyacetamido-1-(2,4-dimethoxybenzyl)-4-oxoazetidine-2-carboxylic acid

HRID 127896

Reaktionsgleichung

Reaktionsgleichung von HRID 127896
C([O-])([O-])=O.[K+].[K+].[O:7]([CH2:14][C:15]([NH:17][C@H:18]1[C:21](=[O:22])[N:20]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:25]=2[O:32][CH3:33])[C@H:19]1[C:34]([O:36]C)=[O:35])=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>O1CCCC1.O>[O:7]([CH2:14][C:15]([NH:17][C@H:18]1[C:21](=[O:22])[N:20]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:25]=2[O:32][CH3:33])[C@H:19]1[C:34]([OH:36])=[O:35])=[O:16])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Komponenten

5

Edukt 2

HCID 11430Potassium CarbonateHCID 70577439Methyl cis-1-(2,4-Dimethoxybenzyl)-3-phenoxyacetamido-4-oxo-2-azetidinecarboxylate

Produkt 1

HCID 70577235cis-3-Phenoxyacetamido-1-(2,4-dimethoxybenzyl)-4-oxoazetidine-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of anhydrous K2CO3 (249 mg, 1.8 mmol) in tetrahydrofuran (8 ml) and water (12 ml) is degassed with argon and then methyl cis-3-phenoxyacetamido-1-(2,4-dimethoxybenzyl)-4-oxoazetidine-2-carboxylate (150 mg, 0.35 mmol) is added. The reaction is stirred 1.5 hours at room temperature, the organic solvent is evaporated and the aqueous layer is acidified and extracted with methylene chloride. The dried extracts are evaporated to give a solid which is recrystallized from ethyl acetate-hexane to give pure cis-3-phenoxyacetamido-1-(2,4-dimethoxybenzyl)-4-oxoazetidine-2-carboxylic acid, mp 169°-170°(d).

Aufarbeitung

  1. customthe organic solvent is evaporated
  2. extractionextracted with methylene chloride
  3. customThe dried extracts are evaporated
  4. customto give a solid which
  5. customis recrystallized from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-0cb885d40da44c1990339dc96c91fd6a
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04257947

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