5-azido-laevulinic acid, method for the production thereof...

Details 5-azido-laevulinic acid, method for the production thereof... 5-azido-laevulinic acid, method for the production thereof...

2008-01-15

2008-01-15

Puttlitz, Karl (Department: 1621)

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

Organic compounds

Carboxylic acids and salts thereof

C562S561000, C562S433000, C552S010000

Reexamination Certificate

active

07319164

ABSTRACT:
The present invention relates to 5-azido levulinic acid, a process for its preparation, its use. Using 5-azido levulinic acid as starting material for the synthesis of 5-amino levulinic acid hydrochloride it is possible to obtain the latter in good yield an in pharmaceutical acceptable quality. 5-Azido levuliniv acid is synthesized in that methyl 5-bromo levulinate and/or methyl 5-chloro levulinate is converted with aqueous hydrochloric acid and as a result of an incomplete bromine/chlorine exchange at the C-5-postion a mixture of 5-chloro levulinic acid and 5-bromo levulinic acid is obtained, and the obtained 5-chloro levulinic acid, a mixture of 5-chloro levulinic acid and 5-bromo levulinic acid and the pure 5-bromo levulinic acid is transferred into 5-azido levulinic acid by conversion with a nucleophilic azide.

REFERENCES:
patent: 5380935 (1995-01-01), Takeya et al.
patent: 5907058 (1999-05-01), Moens
patent: 5945564 (1999-08-01), Takayanagi
patent: 0845457 (1998-06-01), None
Ha et al., Synthetic Communications 24(18) 2557-2562 (1994).
Ha et al., “Selective Bromination of Ketones. A Convenient Synthesis of 5-Aminolevulinic Acid,” Synthetic Communications, 24(18):2557-62 (1994).

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