A conventional route for the synthesis of new oxazolidin-2-one derivatives with β-aminoalanines

Chemical and Pharmaceutical Bulletin

Volumn 52, Issue 10, 2004, Pages 1238-1241

  Fujisaki, Fumiko ^a   Abe, Nobuhiro ^a   Sumoto, Kunihiro ^a  

^a FUKUOKA UNIVERSITY   (Japan)

Author keywords

aminoalanine; Benzoylation; Cyclization; Dehydration; Oxazolidin 2 one; Oxazolidinone

Indexed keywords

3 (3 METHOXYPHENYLMETHYL) 4 (N METHYL N PHENETHYLAMINO)METHYLOXAZOLIDIN 2 ONE; 3 (3 METHOXYPHENYLMETHYL) 4 THIOMORPHOLINOMETHYLOXAZOLIDIN 2 ONE; 3 PHENYLMETHYL 4 (1 PYRROLIDINYLMETHYL)OXAZOLIDIN 2 ONE; 3 PHENYLMETHYL 4 (N METHYL N PHENETHYLAMINO)METHYLOXAZOLIDIN 2 ONE; 3 PHENYLMETHYL 4 PIPERIDINOMETHYLOXAZOLIDIN 2 ONE; 3 PHENYLMETHYL 4 THIOMORPHOLINOMETHYLOXAZOLIDIN 2 ONE; ALANINE DERIVATIVE; BETA AMINOALANINE DERIVATIVE; OXAZOLIDINONE DERIVATIVE; UNCLASSIFIED DRUG; 2,3 DIAMINOPROPIONIC ACID; 2,3-DIAMINOPROPIONIC ACID; BETA ALANINE; DRUG DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS;

BETA-ALANINE; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; OXAZOLIDINONES; STEREOISOMERISM;

EID: 16644373987     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.52.1238     Document Type: Article

References (10)

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6. Camille G. W., "The Practice of Medicinal Chemistry," 2nd ed., Academic Press, San Diego, 2003.
7. Homeyer A. H., U.S. Patent 2399118 (1946) [Chem. Abst., 40, 404084 (1946)].
8. Further modifications of two substituents on the oxazolidin-2-one ring are under investigation to develop a lead compound for new antibacterial agents.
9. The compound having -NHAc functionality as a part of the -NR1R2 group in the target molecule (3) can be obtained with a similar cyclization procedure with diethyl carbonate. However, the procedure for this class of compounds consists of multistage reactions. We will describe the synthesis of these analogues elsewhere.
10. Other amino alcohols (6) were obtained in good to moderate yields (51-83%) using this procedure. However, these compounds contained trace amounts of unknown contaminants. As mentioned in the Discussion, the purifications of these amino alcohols (6) were attributed to a loss of materials, and therefore we used the materials for the next stage without further purification.