Process development and pilot-scale synthesis of cefotetan

Organic Process Research and Development

Volumn 8, Issue 6, 2004, Pages 915-919

  Fujimoto, Masaharu ^a   Maeda, Tetsuya ^a   Okumura, Keisuke ^a   Uda, Mitsuru ^a   Nakamura, Makoto ^a   Kashiwagi, Teruya ^a   Tsunoda, Takashi ^a  

^a ASTELLAS PHARMA INC   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZHYDRYL DERIVATIVE; CEFOTETAN; TRIFLUOROACETIC ACID;

ARTICLE; COST EFFECTIVENESS ANALYSIS; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PILOT STUDY; PROTON NUCLEAR MAGNETIC RESONANCE; TANDEM MASS SPECTROMETRY;

EID: 10044225790     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op049914m     Document Type: Article

References (7)

1. Fujimoto, M. J. Synth. Org. Chem. Jpn. 1997, 57, 374.
2. Iwanami, M.; Maeda, T.; Fujimoto, M.; Nagano, Y.; Nagano, N.; Yamazaki, A.; Shibanuma, T.; Tamazawa, K.; Yano, K. Chem. Pharm. Bull. Jpn. 1980, 28, 2629.
3. Osono, T.; Watanabe, S.; Saito, T.; Gushima, H.; Murakami, K.; Susaki, K.; Takamura, S.; Miyamoto, T.; Oka, Y. J. Antibiot. 1980, 33, 1074.
4. An alternative synthetic route, which involves the coupling of 5 and 2-(tertbutoxycarbonyl carbamoylmethylene)-1,3-dithietane-4-carboxylic acid (11) was developed. 10, produced by the deprotection of the coupling product and the overall yield of this alternative synthetic route, which did not involve any rearrangement reaction, was around 40% from 1.
5. Lunn, W. H. W.; Burchfield, R. W.; Elzey, T. K.; Mason, E. V. Tetrahedron Lett. 1974, 14, 1307.
6. Ahmed, W.; Gerrard, W.; Maladkar, V. K. J. Appl. Chem. 1970, 20, 109.
7. Tsuji, T.; Kataoka, T.; Yoshioka, M.; Sendo, Y.; Nishitani, Y.; Hirai, S.; Maeda, T. Tetrahedron Lett. 1979, 30, 2793.