Process for Developing 3β-[4-(S)-Arylacetylamino-4β-(2-(2-furyl) ethyl]azetidin-2-one: A Carbacephem Key Intermediate

Organic Process Research and Development

Volumn 7, Issue 6, 2003, Pages 933-935

  Kumar, Yatendra ^a   Tewari, Neera ^a   Nizar, Hashim ^a   Rai, Bishwa Prakash ^a   Singh, Shailendra Kumar ^a  

^a RANBAXY RESEARCH LABORATORIES   (India)

Author keywords

[No Author keywords available]

Indexed keywords

3BETA [ACETYLAMINO 4BETA [2 (2 FURYL)ETHYL]AZETIDINE]; AMMONIA; CARBACEPHEM DERIVATIVE; LITHIUM; SODIUM; UNCLASSIFIED DRUG;

ARTICLE; BIRCH REDUCTION; CHEMICAL REACTION; COST EFFECTIVENESS ANALYSIS; REACTION OPTIMIZATION; REDUCTION; SYNTHESIS;

EID: 0346735292     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op034074h     Document Type: Article

References (7)

1. (a) Evans, D. A.; Sjorgren, E. B. Tetrahedron Lett. 1985, 26, 3783.
2. (b) Evans, D. A.; Sjorgren, E. B. Tetrahedron Lett. 1985, 26, 3787.
3. Bodurow, C. C.; Boyer, B. D.; Brennan, J.; Bunnell, C. A.; Burks, J. E.; Carr, M. A.; Doecke, C. W.; Eckrich, T. M.; Fisher, J. W.; Gardner, J. P.; Graves, B. J.; Hines, P.; Hoying, R. C.; Jackson, B. G.; Kinnick, M. D.; Kochert, C. D.; Lewis, J. S.; Luke, W. D.; Moore, L. L.; Morin, J. M., Jr.; Nist, R. L.; Prather D. E.; Sparks, D. L.; Vladuchick, W. C. Tetrahedron Lett. 1989, 30, 2321.
4. Fisher, J. W.; Dunigan, J. M.; Hatfield, L. D.; Hoying, R. C.; Ray, J. E.; Thomas, K. L. Tetrahedron Lett. 1993, 34, 4755.
5. Evans, D. A.; Sjogren, E. A. (Harvard College) E.P. Patent 209,352, 1986.
6. If required, add more ammonium chloride until blue colour discharges. Liquid ammonia should be in excess to dissolve sodium metal completely; add sodium metal in portions.
7. 4 1.36 g/L; adjust pH with orthophosphoric acid). Flow rate: 2 mL/min (gradient acetonitrile: buffer 5:95 to 50:50 in 30 min and 75:25 in 45 min). UV detection at 210 nm. Retention time: 14.5 min.