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 839145

Reaktionsgleichung

Reaktionsgleichung von HRID 839145
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 teemperature 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 ethylacetate to 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 ethylacetate

Quellen und Nachweise

ORD-Eintrag
ord-a09ab6c8851f4498976bb7b89eb2d03f
Quelldatensatz
uspto-grants-1978_06
Patentnummer
US04093804

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