Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acids and salts thereof
Reexamination Certificate
2007-03-26
2010-10-26
Sullivan, Daniel M (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acids and salts thereof
C562S531000
Reexamination Certificate
active
07820858
ABSTRACT:
The present invention provides a method for the synthesis of β2-amino acids. The method also provides methods yielding α-substituted β-amino aldehydes and β-substituted γ-amino alcohols. The present method according to this invention allows for increased yield and easier purification using minimal chromatography or crystallization. The methods described herein are based on an aldehyde aminomethylation which involves a Mannich reaction between an aldehyde and a formaldehyde-derived N,O-acetal (iminium precursor) and a catalyst, such as, for example, L-proline or a pyrrolidine. The invention allows for large scale, commercial preparation of β2-amino acids.
REFERENCES:
patent: 542253 (1931-12-01), None
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Chi, Yonggui et al., “Enantioselective Organocatalytic Aminomethylation of Aldehydes: A Role for Ionic Interactions and Efficient Access to .beta.2-Amino Acids”, Journal of the American Chemical Society, 128(21), 6804 6805 coden, jacsat; issn: 0002-7863, 2006, XP002440654.
Ibrahem, Ismail et al., “Direct catalytic enantilioselective .alpha.-aminomethylation of aldehydes”, Chemistry—A European Journal, 13(2), 683-688 coden: ceujed; issn: 0947-6539, 2007, XP002440655, abstract.
PCT/US2007/064943 International Search Report.
Chi Yonggui
English Emily P.
Gellman Samuel H.
Guo Li
Horne William S.
DeWitt Ross & Stevens S.C.
Leone, Esq. Joseph T.
Sullivan Daniel M
Valenrod Yevegeny
Wisconsin Alumni Research Foundation
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