Synthesis of 7-D-mandel-β-14C-amino-3-{[(1-methyl-1H-tetrazol-5-yl)-thio]methyl}-3-cephem-4-carboxylic acid (cefamandole-14C)
✍ Scribed by H. Minato; T. Nagasaki; Y. Katsuyama; M. Hamada; R. Kiritani
- Publisher
- John Wiley and Sons
- Year
- 1978
- Tongue
- French
- Weight
- 272 KB
- Volume
- 14
- Category
- Article
- ISSN
- 0022-2135
No coin nor oath required. For personal study only.
✦ Synopsis
Cefamandole, 7-D-mandelamino-3-{ [(l-methyl-lH-tetrazo1-5-yl)-thio]methyl}-3-cephem-4-carboxylic acid (I), is a new semisynthetic, parenteral cephalosporin antibiotic with a broad antibacterial spectrum, synthesized by the Lilly Research Laboratories.
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1-(Cyclohexyloxycarbony1oxy)ethyl 7P-[2-(2-aminothiazol-~-yl~acetamido]-3-[[[1-(2-dimethylaminoethyl~-1H-tetrazol-~-yl]thio]methyl]ceph-3-em-4-carboxylate dihydrochloride (SCE-2174), a new orally active cephalos orin, was labeled with carbon-14 starting from [l-lgC] c yc lohexanol (1) . 1 -Chloroe t
## Abstract The title compound 9 was prepared by the route outlined in Scheme I. [^14^C]Thiourea (1) was condensed with ethyl 4‐bromo‐3‐oxo‐2‐methoxyiminoacetate (2), providing ethyl 2‐(2‐amino‐4‐[2‐^14^C]thiazolyl)‐2‐methoxyiminoacetate (3), as the pure Z‐isomer. Saponification gave the amino acid
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## Abstract The synthesis from carbon‐^14^C dioxide of 1, 3‐dihydro‐1‐methyl‐7‐nitro‐5‐phenyl‐2H‐1, 4‐benzodiazepin‐2‐one‐5‐^14^C (I) for use in metabolic studies has been described. The synthesis was achieved by the sequence shown in figure 1. The overall yield of labelled nimetazepam (I) was near