Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1998-11-10
2000-09-12
Barts, Samuel
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
560 39, C07D20708, C07C22928
Patent
active
061180106
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to a technical field wherein in a process for preparing an 1-alkoxycarbonyl-3-phenylpropyl derivative (hereinafter referred also to as an "1-alkoxycarbonyl-3-phenylpropyl derivative (II)") represented by the formula (II): ##STR1## wherein R is an alkyl group, X is -Ala-, -Gly-, -Leu-, -Ile-, -Val-, -Orn-, -Lys- or -Hly-, in which .omega.-amino groups of -Orn-, -Lys- and -Hly- are protected with an acyl protecting group, Y is hydroxyl group which comprises catalytically reducing an 1-alkoxycarbonyl-3-oxo-3-phenylpropyl derivative (hereinafter referred also to as an "1-alkoxycarbonyl-3-oxo-3-phenylpropyl derivative (I)") represented by the formula (I): ##STR2## wherein R, X and Y are the same as the defined above, an 1-alkoxycarbonyl-3-phenylpropyl derivative (II) having little amount of impurities can simply, efficiently and in good productivity be produced and obtained. The 1-alkoxycarbonyl-3-phenylpropyl derivative (II), particularly one having 1S-configuration, is a very useful compound as a drug or an intermediate thereof, particularly various antihypertensive agents such as enalapril and lisinopril, or an intermediate thereof.
BACKGROUND ART
A method of obtaining an 1-alkoxycarbonyl-3-phenylpropyl derivative (II) by catalytically reducing an 1-alkoxycarbonyl-3-oxo-3-phenylpropyl derivative (I) in an alcohol or a solvent containing the alcohol using a transition metal catalyst such as palladium, nickel or platinum as a reduction catalyst is described, for example, in Japanese Examined Patent Publication Nos. 22867/1991 and 4308/1992 and Japanese Unexamined Patent Publication No. 336495/1994.
As the concrete examples of palladium of the reduction catalyst there are, for example, Pd--C, Pd black, and the like. As the concrete examples of nickel there are, for example, Raney Ni, Ni boride, and the like. And as the concrete examples of platinum there are, for example, Pt--C, Pt black, and the like.
For example, Japanese Unexamined Patent Publication No. 336495/1994 discloses an example wherein catalytic reduction is conducted using N-(1-ethoxy-carbonyl-3-oxo-3-phenylpropyl)-L-alanyl-L-proline as a substrate in a water-ethanol mixed solvent (pH 1) containing hydrogen chloride at 20.degree. C. under a pressure of 10 kg/cm.sup.2 for 35 hours. The gazette discloses that the catalytic reduction is preferably conducted at a pH range from 0.5 to 4, particularly pH 1. Incidentally, a method of separating a product is not disclosed.
Japanese Examined Patent Publication No. 4308/1992 discloses an example wherein catalytic reduction is conducted using N.sup.2 -(1-ethoxycarbonyl-3-oxo-3-phenylpropyl)-N.sup.6 -trifluoroacetyl-L-lysine as a substrate in a water-containing ethanol having a hydrogen chloride concentration of about 0.30 N at 40.degree. C. under atmospheric pressure and then N.sup.2 -(1-ethoxycarbonyl-3-phenylpropyl)-N.sup.6 -trifluoroacetyl-L-lysine is separated by crystallizing in an aqueous solution, followed by recrystallizing from water-ethanol.
Further, Japanese Examined Patent Publication No. 22867/1991 discloses an example wherein catalytic reduction is conducted using N-(1-ethoxycarbonyl-3-oxo-3-phenylpropyl)-L-alanine ((1S/1R)=95/5) as a substrate in anhydrous ethanol having a sulfuric acid concentration of about 0.38 N at room temperature under atmospheric pressure, and then N-(1-ethoxycarbonyl-3-phenylpropyl)-L-alanine ((1S/1R)=99/1) is separated through extraction with dichloromethane and crystallization from ethyl acetate.
In the above examples, the above catalytic reduction reaction is generally conducted in an alcohol or a solvent containing an alcohol which contains acid such as formic acid, hydrochloric acid, sulfuric acid or phosphoric acid in a low concentration or no acid, using a substrate in a low concentration of about 0.1 mol/L under a pressure within a range from atmospheric pressure to, for example, at most 50 kg/cm.sup.2.
It is considered that the above catalytic reduction reaction gently proceeds in good yield in a hydrogenation p
Manabe Hajime
Matsumoto Akira
Ueda Yasuyoshi
Barts Samuel
Davis Brian J.
Kaneka Corporation
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