Production of chirally pure amino alcohol intermediates,...

Details Production of chirally pure amino alcohol intermediates,... Production of chirally pure amino alcohol intermediates,...

2009-08-24

2010-06-15

Davis, Brian J (Department: 1621)

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

Organic compounds

Amino nitrogen containing

C564S503000, C549S065000

Reexamination Certificate

active

07737303

ABSTRACT:
A method of selectively preparing a chiral 2S-amino alcohol useful in preparation of an amide sulfonated or acylated with alkyl, substituted aryl or substituted heteroaryl is described. The method involves reacting a di-tert-butyl diazene-1,2-dicarboxylate with a (4S)-4-benzyl-3-[(S)-trifluoromethyl-alkyl substituted alkanoyl]-1,3-oxazolidin-2-one to afford a di-tert-butyl 1-(1S,2S)-([(4S)-4-benzyl-2-oxo-1,3-oxazolidine-3-yl]-carbonyl}-trifluoromethyl-alkyl substituted alkyl)hydrazine-1,2-dicarboxylate. This dicarboxylate is then reduced to yield di-tert-butyl 1-(1S,2S)-[trifluoromethyl-alkyl substituted alkyl]hydrazine-1-(hydroxymethyl)-1,2-dicarboxylate. The resulting product is deblocked with an acid to yield the acid addition salt of (2S,3S)-trifluoro-hydrazino-methyl alkan-1-ol. The acid addition salt of (2S,3S)-trifluoro-2-hydrazino-methyl alkan-1-ol is hydrogenated in the presence of a suitable metal catalyst to yield the amino alcohol (2S,3S)-2-amino-trifluoro-methyl alkan-1-ol HCl.

REFERENCES:
patent: 6610734 (2003-08-01), Kreft
patent: 6657070 (2003-12-01), Resnick
patent: 6800764 (2004-10-01), Kreft
patent: 6878742 (2005-04-01), Kreft
patent: 7166622 (2007-01-01), Kreft
patent: 7300951 (2007-11-01), Kreft
patent: 7399778 (2008-07-01), Resnick
patent: 7547725 (2009-06-01), Kreft
patent: 7550629 (2009-06-01), Porte
patent: 7598422 (2009-10-01), Sellstedt et al.
patent: 2005/0196813 (2005-09-01), Kreft
patent: 2007/0037778 (2007-02-01), Kreft
patent: WO 03/050062 (2003-06-01), None
patent: WO 03/050063 (2003-06-01), None
patent: WO 03/103660 (2003-12-01), None
patent: WO 2004/092155 (2004-10-01), None
patent: WO 2005/073198 (2005-08-01), None
Evans, Electrophilic Azide Transfer to Chiral Enolates. A General Approach to the Asymmetric Synthesis of α-Amino Acids, Journal of the American Chemical Society, vol. 109, pp. 6881-6883, Oct. 1987.
Testa, Prodrugs Revisited: The “Ad Hoc” Approach as a Complement to Ligand Design, Medicinal Research Reviews, vol. 16, No. 3, pp. 233-241, May 1996.
Evans, The Asymmetric Synthesis of α-Amino and α-Hydrazino Acid Derivatives via the Stereoselective Amination of Chiral Enolates with Azodiacarboxylate Esters, Tetrahedron, vol. 44, No. 17, pp. 5525-5540, 1988.
Greene, Greene's Protective Groups in Organic Synthesis, 2ndEdition, pp. 349-362, 1991.
Wuts, Vogel's Textbook of Practical Organic Chemistry, “Qualitative Organic Analysis”, pp. 1129-1133, 1978.
International Search Report issued in International Patent Application No. PCT/US2007/009408 and dated Sep. 17, 2007.
Sellstedt, Office Action issued in U.S. Appl. No. 11/787,962 and dated Oct. 30, 2008.
Sellstedt, Applicants' Response to Office Action issued in U.S. Appl. No. 11/787,962, of record Jan. 29, 2009.

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