7-Amino-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid → (Pivaloyloxy)methyl (6R-trans)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate

HRID 2398962

Reaktionsgleichung

Reaktionsgleichung von HRID 2398962
CN(C)[CH:3]=[O:4].[Na].[NH2:7][CH:8]1[C:15](=[O:16])[N:14]2[CH:9]1[S:10][CH2:11][C:12]([CH3:20])=[C:13]2[C:17]([OH:19])=[O:18].ClC[CH2:23][C:24]([CH3:29])([CH3:28])[C:25]([O-])=[O:26]>C(OC(=O)C)C>[C:25]([O:4][CH2:3][O:18][C:17]([C:13]1[N:14]2[CH:9]([S:10][CH2:11][C:12]=1[CH3:20])[CH:8]([NH2:7])[C:15]2=[O:16])=[O:19])(=[O:26])[C:24]([CH3:29])([CH3:28])[CH3:23]

Komponenten

6

Edukt 4

HCID 18837-Amino-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidHCID 6228DimethylformamideHCID 5360545SodiumHCID 217530474-Chloro-2,2-dimethylbutanoate

Produkt 1

HCID 119617(Pivaloyloxy)methyl (6R-trans)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To 35 ml of dimethylformamide is added 7.5 g of the sodium salt of 7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid and the solution is stirred at room temperature for about 30 minutes after which 8 ml of chloromethylpivalate is added. Stirring is continued at room temperature for about 3 hours. The mixture is diluted with ethylacetate and washed with water. The organic layer is separated, evaporated to dryness, and the residue is recrystallized from ethylacetateto give 7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid pivalyloxymethyl ester.

Aufarbeitung

  1. additionis added
  2. washwashed with water
  3. customThe organic layer is separated
  4. customevaporated to dryness
  5. customthe residue is recrystallized from ethylacetateto

Quellen und Nachweise

ORD-Eintrag
ord-16f4139f2d0d4ddf959bedd62c2c1ae0
Quelldatensatz
uspto-grants-1977_05
Patentnummer
US04026887

Verknüpfte Notizen

Wird geladen…