Reaktion #2377602

ord-0c6ebf9152184cc3b90ca36e34ed5ba2

Reaktionsgleichung

CC(C)(C)OC(=O)C(=[N+]=[N-])C(=O)CO[C@H]1NC(=O)[C@@H]1NC(=O)c1ccccc1
tert.-butyl 4-[3(R)-benzoylamino-2-azetidinon-4-(R)-yloxy]-2-diazo-3-oxo-butyrate
→
CC(C)(C)OC(=O)C1=C(O)CO[C@@H]2[C@@H](NC(=O)c3ccccc3)C(=O)N12
title compound
Ausbeute 17.0%
CC(C)(C)OC(=O)C1=C(O)CO[C@@H]2[C@@H](NC(=O)c3ccccc3)C(=O)N12
tert.-Butyl (6R, 7R)-7-benzoylamino-3-hydroxy-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
Ausbeute 17.0%

Edukte

CC(C)(C)OC(=O)C(=[N+]=[N-])C(=O)CO[C@H]1NC(=O)[C@@H]1NC(=O)c1ccccc1
tert.-butyl 4-[3(R)-benzoylamino-2-azetidinon-4-(R)-yloxy]-2-diazo-3-oxo-butyrate

Reagenzien

[Hg]
mercury

Lösungsmittel

C1CCOC1.c1ccccc1
benzene tetrahydrofuran

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Filtrationfilter
  2. 2
    SonstigeThe solvent was evaporated off in vacuo
  3. 3
    Sonstigethe residue was purified by chromatography on 8 g of silica gel (toluene:ethyl acetate 35:65)

Vorschrift

An anhydrous and degassed solution of 78 mg (0.2 mmol) of tert.-butyl 4-[3(R)-benzoylamino-2-azetidinon-4-(R)-yloxy]-2-diazo-3-oxo-butyrate in 25 ml of benzene:tetrahydrofuran 3:1 was irradiated in a nitrogen atmosphere at 20° C. for 1 hour with a 450 W mercury vapour lamp with a Pyrex filter. The solvent was evaporated off in vacuo and the residue was purified by chromatography on 8 g of silica gel (toluene:ethyl acetate 35:65). 12 mg (17%) of the title compound were obtained as a colorless rigid foam.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04616084uspto-grants-1986_10