Catalytic transfer hydrogenolysis of 4-nitrobenzyl esters of cephalosporins

Tetrahedron Letters

Volumn 39, Issue 16, 1998, Pages 2405-2408

  Albanese, Domenico ^a   Leone, Mario ^b   Penso, Michele ^a   Seminati, Monica ^a   Zenoni, Maurizio ^b  

^a CNR   (Italy)

^b ACS Dobfar   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CEPHALOSPORIN DERIVATIVE; CEPHEM DERIVATIVE; FORMIC ACID; NITROBENZOIC ACID DERIVATIVE; PHOSPHINIC ACID DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; ISOMERISM; SYNTHESIS;

EID: 0032537211     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00210-X     Document Type: Article

References (16)

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4. 3. a) Kukolja, S.; Lammert, S. R.; Gleissner, M. R. B.; Ellis, A. I. J. Am. Chem. Soc. 1976, 98, 5040-5041.
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6. nd ed. John Wiley & Sons, New York, 1991, pp. 258.
7. 3b with an equimolar amount of the appropriate acyl chloride at room temperature in dichlorometha ne, in the presence of a four-fold excess of solid potassium hydrogen carbonate.
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11. 9. Namikoshi, M.; Kundu, B.; Rinehart, K. L. J. Org. Chem. 1991, 56, 5464-5466.
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13. 11. Jackson, A. E.; Johnstone, R. A. W. Synthesis 1976, 685-686.
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16. 3COOH (20 mmol) were added to a stirred suspension of ester 1a (2 mmol) in anhydrous MeOH (25 ml) under a nitrogen atmosphere. After completion of the reaction (TLC or HPLC control), the catalyst was removed by filtration through celite and the filtrate evaporated to dryness. The residue was dissolved in a saturated sodium chloride solution, some insoluble material filtered, and acidified to pH 1 with 10% HCl. The acid 2a was isolated by filtration as a white crystalline compound. Products 1,2a-d are known compounds and all spectrosco pical and analytical data match those reported in the literature (see for example U. S. Patent 3,925,372; Chem. Abstr., 84, 105620q. German. Offen. 2,408,698 Chem Abstr., 82, 4278n. German. Offen. 2,331,133 Chem Abstr., 80, 83019).