Triphenylphosphine → Pivaloyloxymethyl 3-acetylthio-7-oxo-4-thia-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate

HRID 370504

Reaktionsgleichung

Reaktionsgleichung von HRID 370504
[C:1]([S:4][C:5]1[S:12]S[CH:10]2[N:7]([C:8](=[O:13])[CH2:9]2)[C:6]=1[C:14]([O:16][CH2:17][O:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[O:15])(=[O:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[2H]C(Cl)(Cl)Cl>[C:1]([S:4][C:5]1[S:12][CH:10]2[N:7]([C:8](=[O:13])[CH2:9]2)[C:6]=1[C:14]([O:16][CH2:17][O:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[O:15])(=[O:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 11776TriphenylphosphineHCID 20275776Pivaloyloxymethyl 3-acetylthio-8-oxo-4,5-dithia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylate

Produkt 1

HCID 20275786Pivaloyloxymethyl 3-acetylthio-7-oxo-4-thia-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 71583Chloroform-DLösungsmittel

Versuchsvorschrift

To a solution of 22 mg of pivaloyloxymethyl 3-acetylthio-8-oxo-4,5-dithia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylate in deuterochloroform were added 14.7 mg of triphenylphosphine. TLC analysis indicated complete conversion of the starting material and the product was shown by IR and NMR analysis to be the title compound. This product was isolated by chromatography on silica gel using ethyl acetate/hexane mixtures as solvent. The yield of product was 13 mg (65%).

Quellen und Nachweise

ORD-Eintrag
ord-57538fc609964c979ab6b6e865997721
Quelldatensatz
uspto-grants-1985_07
Patentnummer
US04526718

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