p-Toluenesulfonic acid → cis-2-Azidomethyl-3-t-butoxycarbonylamino-4-oxoazetidine

HRID 2050387

Reaktionsgleichung

Reaktionsgleichung von HRID 2050387
[BH4-].[Na+].[C:3]([O:7][C:8]([NH:10][C@H:11]1[C:14](=[O:15])[NH:13][C@H:12]1[C:16](OC)=O)=[O:9])([CH3:6])([CH3:5])[CH3:4].OCC1CCN1.CC1C=CC(S(O)(=O)=O)=CC=1.[N-:37]=[N+:38]=[N-:39].[Na+]>>[N:37]([CH2:16][C@H:12]1[C@@H:11]([NH:10][C:8]([O:7][C:3]([CH3:4])([CH3:5])[CH3:6])=[O:9])[C:14](=[O:15])[NH:13]1)=[N+:38]=[N-:39]

Komponenten

6

Edukt 5

HCID 6101p-Toluenesulfonic acidHCID 33557Sodium AzideHCID 4311764Sodium borohydrideHCID 15251628(Azetidin-2-yl)methanolHCID 70428372Methyl cis-3-t-butoxycarbonylamino-4-oxoazetidine-2-carboxylate

Produkt 1

HCID 86734331cis-2-Azidomethyl-3-t-butoxycarbonylamino-4-oxoazetidine

Versuchsvorschrift

Sodium borohydride reduction of methyl cis-3-t-butoxycarbonylamino-4-oxoazetidine-2-carboxylate as described in Preparation 3, followed by conversion of the 2-hydroxymethylazetidine product to the p-toluenesulfonate derivative, mp 160°-162°(d), and the reaction of the derivative with sodium azide as described in Preparation 4 gives the title compound.

Aufarbeitung

  1. customas described in Preparation 4

Quellen und Nachweise

ORD-Eintrag
ord-93491f2987e94080b7fd9cecc5052b19
Quelldatensatz
uspto-grants-1980_04
Patentnummer
US04200572

Verknüpfte Notizen

Wird geladen…