Stereoselective nucleophilic substitution of oxazepam and racemization in acidic methanol and ethanol

Chirality

Volumn 8, Issue 2, 1996, Pages 214-223

  Yang, Shen K ^a   Bao, Ziping ^a   Shou, Magang ^b  

^a Uniformed Services University of the Health Sciences and the Walter Reed National Military Medical Center   (United States)

^b NATIONAL CANCER INSTITUTE   (United States)

Author keywords

circular dichroism spectropolarimetry; mass spectrometry; oxazepam; racemization; reversed phase and chiral stationary phase high performance liquid chromatography

Indexed keywords

ALCOHOL; HYDROXYL GROUP; METHANOL; OXAZEPAM; TEMAZEPAM;

ARTICLE; CHIRALITY; CIRCULAR DICHROISM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PRIORITY JOURNAL; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STEREOCHEMISTRY;

ANTI-ANXIETY AGENTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ETHANOL; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; METHANOL; OXAZEPAM; STEREOISOMERISM;

EID: 0029879614     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1996)8:2<214::AID-CHIR7>3.0.CO;2-I     Document Type: Article

References (21)

1. Top 200 drugs of 1986. Pharmacy Times, April 1987.
2. Bell, S. C., McCaully, R.J., Gochman, C., Childress, S.J., Gluckman. M.I. 3-Substituted 1,4-benzodiazepin-2-ones. J. Med. Chem. 11:457-461, 1968.
3. Yang, S.K. Acid-catalyzed ethanolysis of temazepam in anhydrous and aqueous ethanol solutions. J. Pharm. Sci. 83:898-902, 1994.
4. Yang, T.J., Yang, S.K. Acid-catalyzed reaction of ethanol and oxazepam and its pharmacological consequence. J. Food Drug Anal. 1995 3:173-183.
5. Yang, S.K. Substitution and racemization of 3-hydroxy- and 3-alkoxy-1,4-benzodiazepines in acidic aqueous solutions. Chirality 7:365-375, 1995.
6. Yang, S.K. Acid-catalyzed stereoselective heteronucleophilic substitution and racemization of 3-O-methyloxazepam and 3-O-ethyloxazepam, Chirality 6:175-184, 1994.
7. Yang, S.K. Stereosetectivity in acid-catalyzed heteronucleophitic substitution of enantiomeric 3-O-methyloxazepam and 3-O-ethyloxazepam. Chirality 7:34-39, 1995.
8. Yang, S.K., Lu, X.L. Nucleophilic substitution and racemization of 3-ethoxy-N-desmethyldiazepam enantiomers in acidic ethanol. J. Food Drug Anal. 1:23-34, 1993.
9. Yang, S.K., Lu, X.L. Acid-catalyzed nucleophilic substitution and raceraization of 3-methoxy-N-desmethyldiazepam enantiomers in methanol. Chirality 5:91-96, 1993.
10. Yang, S.K., Lu, X.L. Stereoselective homonucleophilic substitution of 3-O-methyl and 3-O-ethyloxazepam enantiomers by chiral stationary phase high-performance liquid chromatography. J. Pharm. Biomed. Anal. 11:1181-1188, 1993.
11. Sunjic, V., Lisini, A., Kovac, T., Belin, B., Kajfez, F., Klasinc, L. Chiral 1,4-benzodiazepines. X. Further investigations of configurational stability of the chiral centre c(3). Croat. Chem. Acta 49:505-515, 1977.
12. Sunjic, V., Oklobdzija, M., Lisini, A., Sega, A., Kajfez, F., Srzic, D., Klasinc, L. Chiral 1,4-benzodiazepines. XI. Kinetics of degenerate nucleophilic exchange of C(3)-hydroxy group. Tetrahedron Lett. 35:2531-2537, 1979.
13. Yang, S.K., Yang, T.J., Pu, Q.L. Reactions of temazepam in acidic aqueous solution via oxygen 18-labeled product analysis by mass spectrometry. Anal. Chim. Acta 83:307-316, 1995.
14. Yang, S.K., Lu, X.L. Racemuation kinetics of enantiomenc oxazepams and stereoselective hydrolysis of enantiomeric oxazepam 3-acetates in rat liver microsomes and brain homogenate. J. Pharm Sci. 78:789-795, 1989.
15. Barrett, J., Smyth, W.F., Davidson, I.E. An examination of acid-base equilibria of 1,4-benzodiazepines by spectrophotometry. J. Pharm. Pharmacol. 25:387-393, 1973.
16. Peterson, P.E. Equivalent scales for correlation using two solvent parameters. In: Nucleophilicity. Advances in Chemistry Series 215. Harris, J.M., Mc Manus, S.P., eds. Washington, DC: American Chemical Society, 1987: 299-314.
17. Yang, S.K., Lu, X.L. Resolution and stability of oxazepam enantiomers. Chirality 4:443-446, 1992.
18. Stromar, M., Sunjic, V., Kovac, T., Klasinc, L., Kajfez, F. Chiral 1,4-benzodiazepines. VIII. Concerning the rate of H/D exchange and optical stability of the chiral centre C(3). Croatica Chem. Acta 46:265-274, 1974.
19. Blaschke, G., Markgraf, H. Chlortalidon-, chlortalidon-methylether-und oxazepam-enantiomere. Chem. Ber. 113:2031-2035, 1980.
20. Srzic, D., Klasinc, L., Belin, B., Kajfez, F., Sunjic, V. Kinetics of degenerate nucleophilic exchange of C(3)-hydroxy group in 1-methyl-3-hydroxy-5-phenyl-7-chloro-2H-1,4-benzodiazepin-2-one. Recent Dev, Mass Spectr. Biochem. Med. 2; 149-153, 1979.
21. Bell, S.C., Childress, S.J. Additional rearrangements of S-phenyl-1,4-benzodiazepines. J. Org. Chem. 29:506-507, 1964.