PRODUCTION OF 3-AMIONO-2-OXO-1-HALOGENOPROPANE DERIVATIVE

Title:

PRODUCTION OF 3-AMIONO-2-OXO-1-HALOGENOPROPANE DERIVATIVE

Document Type and Number:

Japanese Patent JP3855323

Kind Code:

B2

Abstract:

PROBLEM TO BE SOLVED: To obtain a compound as an equivalent material of α-aminoalcohol derivative important as an intermediate for HIV protease inhibitor as a sort of enzyme-inhibitor and convertible into 3-amino-1,2-epoxypropanes.
SOLUTION: A compound of formula I (Rs is H, a 1-10c alkyl or a 6-15C aryl, etc.; P1 and R2 are each H or an amino protecting group, etc.; E1 is an ester residue of a 1-10C alkoxy, etc.) is reacted with an alkali metal enolate of an acetate ester to obtain a compound of formula II (R1 is a 1-10C alkyl or a 6-15C aryl, etc.). A halogenating reagent is applied to the resultant compound and its 2-position is halogenated to obtain 4-amino-3-oxo-2- halogenobutanoic acid ester derivative of formula III (X is a halogen other than F). Then, the resultant derivative is hydrolyzed and decarboxylated to obtain the objective compound of formula IV in a short and safe process in a high yield.

Inventors:

Yutaka Honda
Satoshi Katayama
Kunisuke Izawa
Masakazu Nakazawa
Takayuki Suzuki
Naoko Kanno

Application Number:

JP30605196A

Publication Date:

December 06, 2006

Filing Date:

November 18, 1996

Export Citation:

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Assignee:

AJINOMOTO CO.,LTD.

International Classes:

C07C225/16; C07D307/33; C07C221/00; C07C229/34; C07C269/06; C07C271/16; C07C271/18; C07C271/22; C07C311/16; C07C323/25; C07C323/58; C07D303/36; (IPC1-7): C07C225/16; C07C221/00; C07C269/06; C07C271/16; C07C271/18; C07C271/22; C07C311/16; C07C323/25; C07C323/58; C07D303/36; C07D307/33; //C07C229/34; C07M7:00

Domestic Patent References:

JP52097994A
JP5286900A

Foreign References:

US5021454

Other References:

Journal of Organic Chemistry,1990年,55(1),p.386-388

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