Reaktion #1666065

ord-29bfefe8ae484e2dba774730cf38eac9

Reaktionsgleichung

CC(C)(C)OC(=O)C(N1C(=O)C(NC(c2ccccc2)(c2ccccc2)c2ccccc2)C1SCC(=O)Cc1ccccc1)=P(c1ccccc1)(c1ccccc1)c1ccccc1
1-(1-t-Butoxycarbonyl-1-triphenylphosphoranylidenemethyl)-3-(triphenylmethylamino)-4-(3-phenyl-2-oxopropylthio)azetidin- 2-one
→
CC(C)(C)OC(=O)C1=C(Cc2ccccc2)CS[C@@H]2C(NC(c3ccccc3)(c3ccccc3)c3ccccc3)C(=O)N12
( III )
Ausbeute 62.7%
CC(C)(C)OC(=O)C1=C(Cc2ccccc2)CS[C@@H]2C(NC(c3ccccc3)(c3ccccc3)c3ccccc3)C(=O)N12
t-Butyl 3-benzyl-7-triphenylmethylamino-3-cephem-4-carboxylate
Ausbeute 62.7%

Edukte

CC(C)(C)OC(=O)C(N1C(=O)C(NC(c2ccccc2)(c2ccccc2)c2ccccc2)C1SCC(=O)Cc1ccccc1)=P(c1ccccc1)(c1ccccc1)c1ccccc1
1-(1-t-Butoxycarbonyl-1-triphenylphosphoranylidenemethyl)-3-(triphenylmethylamino)-4-(3-phenyl-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-phenyl-2-oxopropylthio)azetidin- 2-one (331 mg) was refluxed in dry dioxan (15 ml) under nitrogen for 25 hours. Evaporation of the solvent and chromatography of the residue on silica gave (III) (141 mg). νmax (CHCl3) 3480, 1775, 1710, 1630 cm-1 δ ppm (CDCl3) 1.5 (s.9H), 2.95 (d.1H. J= 10Hz, D2O exchange), 3.00 (centre of AB quartet), 3.68 (centre of AB quartet, J= 15Hz), 4.25 (d. 1H. J= 5Hz), 4.70 (q. 1H, J= 5Hz, 10Hz, collapsing to a doublet, J= 5Hz, on D2O exchange), 7.1-7.7 (m, 20H).

Quelle

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