Water → HCID 23335851, Verbindung

HRID 904029Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 904029
O1C2C=CC(CC(O)=O)=CC=2CC1.S(Cl)(Cl)=O.[CH2:18]([O:20][S:21]([CH:24]([C:28]1[CH:29]=[CH:30][C:31]2[O:35][CH2:34][CH2:33][C:32]=2[CH:36]=1)[C:25]([OH:27])=O)(=[O:23])=[O:22])[CH3:19].O.[NH2:38][CH:39]1[C:46](=[O:47])[N:45]2[CH:40]1[S:41][CH2:42][C:43]([CH3:51])=[C:44]2[C:48]([OH:50])=[O:49].C(=O)(O)[O-].[Na+]>CCOCC.C(OCC)(=O)C>[CH2:18]([O:20][S:21]([CH:24]([C:28]1[CH:29]=[CH:30][C:31]2[O:35][CH2:34][CH2:33][C:32]=2[CH:36]=1)[C:25]([NH:38][CH:39]1[C:46](=[O:47])[N:45]2[CH:40]1[S:41][CH2:42][C:43]([CH3:51])=[C:44]2[C:48]([OH:50])=[O:49])=[O:27])(=[O:22])=[O:23])[CH3:19]

Komponenten

9

Edukt 6

HCID 962WaterHCID 18837-Amino-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 27374552,3-Dihydro-5-benzofuranacetic acidHCID 23335847HCID 23335847, Verbindung

Produkt 1

HCID 23335851HCID 23335851, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

α-Ethoxysulfonyl(2,3-dihydro-5-benzofuranyl acetic acid (5mmole) in 50 ml of dry ether is reacted with about 5.5 mole of thionyl chloride at 20° C. for 4 hours. At the end of this time the solvent is removed to insure that all of the thionyl chloride and hydrochloric acid is removed. The residue is then redissolved in 10 ml of ether. This ether solution is added to 10 ml of water containing 5 mmole of 7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid and 10 mmole of sodium bicarbonate. The temperature of the aqueous solution is about 10° C. After stirring for about 2 hours, the pH is adjusted to about 2. Ethyl acetate is added, the mixture is thoroughly agitated and the layers separated. The organic layer is dried over magnesium sulfate, filtered and evaporated to give the title compound.

Aufarbeitung

  1. customAt the end of this time the solvent is removed
  2. customis removed
  3. dissolutionThe residue is then redissolved in 10 ml of ether
  4. customis about 10° C
  5. stirringthe mixture is thoroughly agitated
  6. customthe layers separated
  7. dry with materialThe organic layer is dried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-023ae5bd5b6f42399f5eb6adbb3b79df
Quelldatensatz
uspto-grants-1980_10
Patentnummer
US04229575

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