Title:
PRODUCTION OF OPTICALLY ACTIVE 2-HYDROXY-4-ARYLBUTYRIC ACID OF ITS ESTER
Document Type and Number:
Japanese Patent JP3915015
Kind Code:
B2
Abstract:
PROBLEM TO BE SOLVED: To obtain the subject compound useful as a synthetic intermediate for enalapril, cilazapril, etc., which are excellent antihypertensive agents.
SOLUTION: An optically active acyloxysuccinic anhydride represented by formula II (R1 is a 2-7C straight-chain, branched chain, a cyclic aliphatic acyl group, etc.) is reacted with a 4-10C aromatic compound in the presence of a catalyst (a Lewis acid such as anhydrous aluminum chloride) to provide an optically active 2-acyloxy-4-oxo-4-arylbutyric acid represented by formula III. The catalytic reducing reaction of the carbonyl group at the 4-position and the eliminating reaction of the acyl group in the resultant compound represented by formula III are further carried out to afford the objective compound represented by formula I (R2 is a 4-10C aryl; * is asymmetric carbon atom), e.g. an optically active 2-hydroxy-4-arylbutyric acid. Both the compounds represented by formulas I and II are the (R)-isomers at this time.
Inventors:
Masahiko Kurauchi
Yoshima Hagiwara
Hiroyuki Matsueda
Takashi Nakano
Kunisuke Izawa
Yoshima Hagiwara
Hiroyuki Matsueda
Takashi Nakano
Kunisuke Izawa
Application Number:
JP19264896A
Publication Date:
May 16, 2007
Filing Date:
June 19, 1996
Export Citation:
Assignee:
AJINOMOTO CO.,LTD.
International Classes:
B01J27/125; C07B53/00; C07C59/205; C07B61/00; C07C51/083; C07C51/377; C07C67/08; C07C67/293; C07C67/317; C07C67/343; C07C69/157; C07C69/732; (IPC1-7): C07C59/205; B01J27/125; C07B53/00; C07C51/083; C07C67/08; C07C67/293; C07C67/317; C07C69/157; C07C69/732; //C07B61/00; C07M7:00
Domestic Patent References:
JP5070715A | ||||
JP52116485A | ||||
JP56167636A |
Foreign References:
AT401513B |
Other References:
Tomisawa, Kazuyuki; Kameo, Kazuya; Matsunaga, Tohru; Saito, Shiuji; Hosoda, Kazuaki; Asami, Yumiko; Sota, Kaoru,Studies on hypolipidemic agents. 2. 3-(4-Phenoxybenzoyl)propionic acid rivatives,Chemical and Pharmaceutical Bulletin,1985年,33(6),2386-94
J. David,Preparation of diastereomeric 2-deuterio-3-hydroxybutyrate. A general method for hydrogenation of b-acyloxy-a,b-unsaturated crotonates, Rozzell,Tetrahedron Letters,1982年,23(17),1767-70
J. David,Preparation of diastereomeric 2-deuterio-3-hydroxybutyrate. A general method for hydrogenation of b-acyloxy-a,b-unsaturated crotonates, Rozzell,Tetrahedron Letters,1982年,23(17),1767-70
Attorney, Agent or Firm:
Masao Shimokoshi