Process for the manufacture of (4,5)-trans-oxazolidines

Details Process for the manufacture of (4,5)-trans-oxazolidines Process for the manufacture of (4,5)-trans-oxazolidines

1996-10-30

1997-09-23

Richter, Johann

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548230, C07D26320

Patent

active

056706537

ABSTRACT:
Compounds containing a (4,5)-cis-2-oxo-oxazolidine ring are isomerized to the corresponding (4,5)-trans-2-oxo-oxazolidine by treating the cis compound with a strong base.

REFERENCES:
patent: 5495025 (1996-02-01), Hilpert
Matsumoto, et al, A Steroselective Synthesis Of Cyclohexylnorstatine, The Key Component Of A Renin Inhibitor, Tetrahedron Letters, vol. 31, No. 29, pp 4175-4176 (1990).
Kobayashi, et al, Novel Synthesis Of Three Types of C-Terminal Components Of Renin Inhibitors From Unnatural (2S,3S)-Tartaric Acid, Chem. Pharm. Bull. vol. 39, No. 10, pp. 2550-2555 (1991).
Melon et al, Enantiomerically pure 3-amino-2-hydroxy and 5-amino-4-hydroxy acids from D-isoascorbic acid, Bull. Soc. Chim. Fr. vol. 129, p. 585-592, 1992.
Herranz et al, An Improved One-Pot Method for the Stereoselective Synthesis of the (2S,3R)-3-Amino-2-hydroxy Acids: Key Intermediates for Bestatin and Amastatin, J. Org. Chem. vol. 55, pp. 2232-2234, 1990.
Patel et al, Activated Ketone Based Inhibitors of Human Renin, Journal of Medicinal Chemistry, vol. 36, No. 17, pp. 2431-2447, 1993.
Magnus et al, New Strategy for the Synthesis of the Taxane Diterpenes:Formation of the A-Ring via Nitro-aldol and Aldol Reactions, J. Chem. Soc., Chem. Commun., pp. 1933-1934, 1995.
Iizuka et al, Orally Potent Human Renin Inhibitors from Angiotensinogen Transition State: Design, Synthesis, and Mode of Interaction, J. Med. Chem. vol. 33, pp. 2707-2714, 1990.

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