Tetrabutylammonium (2S,3S)-3-{[(benzyloxy)carbonyl]amino}-2-methyl-4-oxoazetidine-1-sulfonate → (2S,3S)-3-Amino-2-methyl-4-oxo-1-azetidinesulfonic acid

HRID 1732082Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1732082
C([N+](CCCC)(CCCC)CCCC)CCC.C(OC([NH:28][C@H:29]1[C@H:32]([CH3:33])[N:31]([S:34]([O-:37])(=[O:36])=[O:35])[C:30]1=[O:38])=O)C1C=CC=CC=1>C(O)C.[Pd]>[NH2:28][C@H:29]1[C@H:32]([CH3:33])[N:31]([S:34]([OH:37])(=[O:35])=[O:36])[C:30]1=[O:38]

Komponenten

4

Edukt 1

HCID 13631608Tetrabutylammonium (2S,3S)-3-{[(benzyloxy)carbonyl]amino}-2-methyl-4-oxoazetidine-1-sulfonate

Produkt 1

HCID 133361(2S,3S)-3-Amino-2-methyl-4-oxo-1-azetidinesulfonic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

(3S-trans)-3-[(Benzyloxycarbonyl)amino]-4-methyl-2-oxo-1-azetidinesulfonic acid tetra-n-butylammonium salt is dissolved in 250 ml of ethanol and 0.8 g of 5% palladium on charcoal is added. Hydrogen is bubbled through the stirred mixture for 90 minutes and the catalyst is filtered out. The addition of 12 ml of formic acid causes an immediate precipitation of the title compound which is filtered and dried. A second crop of the title compound is obtained upon concentration of the filtrate and the addition of more formic acid, yielding a total of 1.3 g of the title compound.

Aufarbeitung

  1. customHydrogen is bubbled through the stirred mixture for 90 minutes
  2. filtrationthe catalyst is filtered out
  3. additionThe addition of 12 ml of formic acid
  4. customan immediate precipitation of the title compound which
  5. filtrationis filtered
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-0ddf94d3feba4328923abfefe7617757
Quelldatensatz
uspto-grants-1986_11
Patentnummer
US04625022

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