Reaktion #1666068

ord-96b5fe5c7edd4aebb5d079acd3a95e82

Reaktionsgleichung

CC(C)(C)OC(=O)C(N1C(=O)C(NC(c2ccccc2)(c2ccccc2)c2ccccc2)C1SCC(=O)Cc1ccc(F)cc1)=P(c1ccccc1)(c1ccccc1)c1ccccc1
1-(1-t-butoxycarbonyl-1-triphenylphosphoranylidenemethyl)-3-(triphenylmethylamino)-4-(3-p-fluorophenyl-2-oxopropylthio)azetidin-2-one
→
CC(C)(C)OC(=O)C1=C(Cc2ccc(F)cc2)CS[C@@H]2C(NC(c3ccccc3)(c3ccccc3)c3ccccc3)C(=O)N12
( IX )
Ausbeute 75.5%
CC(C)(C)OC(=O)C1=C(Cc2ccc(F)cc2)CS[C@@H]2C(NC(c3ccccc3)(c3ccccc3)c3ccccc3)C(=O)N12
t-Butyl 3-p-fluorobenzyl-7-triphenylmethylamino-3-cephem-4-carboxylate
Ausbeute 75.5%

Edukte

CC(C)(C)OC(=O)C(N1C(=O)C(NC(c2ccccc2)(c2ccccc2)c2ccccc2)C1SCC(=O)Cc1ccc(F)cc1)=P(c1ccccc1)(c1ccccc1)c1ccccc1
1-(1-t-butoxycarbonyl-1-triphenylphosphoranylidenemethyl)-3-(triphenylmethylamino)-4-(3-p-fluorophenyl-2-oxopropylthio)azetidin-2-one

Reagenzien

Keine

Lösungsmittel

C1COCCO1
dioxan

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeEvaporation of the solvent and chromatography of the residue on silica

Vorschrift

1-(1-t-butoxycarbonyl-1-triphenylphosphoranylidenemethyl)-3-(triphenylmethylamino)-4-(3-p-fluorophenyl-2-oxopropylthio)azetidin-2-one (253 mg) was refluxed in dry dioxan (25 ml) under nitrogen for 24 hours. Evaporation of the solvent and chromatography of the residue on silica gave (IX) as a white solid (131 mg). νmax (CHCl3) 1775, 1715 cm-1 δ ppm (CDCl3) 1.52 (s, 3H), 3.01 (q, J = 17 Hz, 2H), 2.66- 3.12 (1H, exchange, D2O, 3.63 (q, J = 15Hz, 2H). 4.28 (d, J = 4.5Hz, 1H), 4.71 (multiplet collapsing to d, J = 4.5Hz on D2O exchange, 1H), 6.77-7.58 (m, aromatic).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US03939157uspto-grants-1976_02