p-Toluenesulfonic acid → Methyl (2R,3R)-3-amino-4-oxoazetidine-2-carboxylate

HRID 1862877Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1862877
[N:1]([C@H:4]1[C:7](=[O:8])[NH:6][C@H:5]1[C:9]([O:11][CH3:12])=[O:10])=[N+]=[N-].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C.[Pd]>[NH2:1][C@H:4]1[C:7](=[O:8])[NH:6][C@H:5]1[C:9]([O:11][CH3:12])=[O:10]

Komponenten

5

Edukt 2

HCID 6101p-Toluenesulfonic acidHCID 13566680Methyl (2R,3R)-3-azido-4-oxoazetidine-2-carboxylate

Produkt 1

HCID 14230520Methyl (2R,3R)-3-amino-4-oxoazetidine-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of methyl cis-3-azido-4-oxoazetidine-2-carboxylate (8.5 g, 50 mmol) and an equivalent of p-toluenesulfonic acid in 200 ml of ethanol is hydrogenated for 3 hours over 1 g of 10% Pd on carbon at 40 psi. The solution is filtered and the filtrate is evaporated to title product or the tosylate salt which can be converted to the free base by standard methods.

Aufarbeitung

  1. filtrationThe solution is filtered
  2. customthe filtrate is evaporated to title product

Quellen und Nachweise

ORD-Eintrag
ord-c1e3ce86c9d24ae5aad778cf962eae29
Quelldatensatz
uspto-grants-1979_09
Patentnummer
US04166816

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