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(12) United States Patent (10) Patent No.: US 8,017,797 B2 Minowa Et Al

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(12) United States Patent (10) Patent No.: US 8,017,797 B2 Minowa Et Al USO08017797B2 (12) United States Patent (10) Patent No.: US 8,017,797 B2 Minowa et al. (45) Date of Patent: Sep. 13, 2011 (54) METHOD FOR PRODUCING FOREIGN PATENT DOCUMENTS PHOSPHORUS-CONTAINING O-KETOACD EP O121226 10, 1984 EP O249.188 12/1987 (75) Inventors: Nobuto Minowa, Kanagawa (JP); JP 56-092897 T 1981 JP 59-1841.96 10, 1984 Nozomu Nakanishi, Kanagawa (JP); JP 64-27485 1, 1989 Masaaki Mitomi, Kanagawa (JP) JP 5-247068 9, 1993 JP 2003-528572 9, 2003 (73) Assignee: Meiji Seika Kaisha Ltd., Tokyo (JP) JP 2004-245,963 9, 2004 OTHER PUBLICATIONS (*) Notice: Subject to any disclaimer, the term of this patent is extended or adjusted under 35 Zeiss, H.-J. "Enantioselective Synthesis of Both Enantiomers of U.S.C. 154(b) by 202 days. Phosphinothricin via Asymmetric Hydrogenation of O-Acylamido Acrylates”.J. Org. Chem., vol. 56, pp. 1783-1788, 1991. Weissermel et al., “Advances in Organophsphorus Chemistry Based (21) Appl. No.: 12/530,022 on Dichloro(methyl)phosphane' Angew. Chem. Int. Ed. Engl., vol. 20, pp. 223-233, 1981. (22) PCT Filed: Mar. 21, 2008 Zu. Obshch. Khim. vol. 46, pp. 243-246, 1977. Gazizov et al., Zh. Obshch. Khim. (J. General Chemistry of the (86). PCT No.: PCT/UP2008/0552O6 USSR), vol. 42, pp. 1718-1721, 1972. English language Abstract of EP 0121226, corresponding to JP S371 (c)(1), 59-184196, 1984. (2), (4) Date: Sep. 4, 2009 English language Abstract of DE 19919848, corresponding to JP 2003-528572, 2003. U.S. Appl. No. 12/529,953 to Kurihara et al., entitled “Process for (87) PCT Pub. No.: WO2008/117733 Producing Phosphorus-Containing Dehydroamino Acid' which PCT Pub. Date: Oct. 2, 2008 application is the National Stage of PCT/JP2008/055032, filed Mar. 19, 2008. International Search Report for PCT/JP2008/055206, mailed Apr. (65) Prior Publication Data 15, 2008. US 201O/OO63313 A1 Mar. 11, 2010 International Preliminary Report on Patentability for PCT/JP2008/ 055206, issued Sep. 29, 2009. (30) Foreign Application Priority Data Primary Examiner — Peter O Sullivan (74) Attorney, Agent, or Firm — Greenblum & Bernstein, Mar. 23, 2007 (JP) ................................. 2007-076541 P.L.C. (51) Int. Cl. (57) ABSTRACT C07C 67/00 (2006.01) A method for efficiently producing 4-(hydroxymethylphos (52) U.S. Cl. ................ 560/51; 560/76; 560/78; 560/81; phinyl)-2-oxobutanoic acid, useful as a production interme 560/103: 560/106; 560/109; 560/130; 560/146; diate of herbicide L-AMPB. The method comprises using a 560/174; 560/176; 560/190; 560/191 compound represented by the below formula (4): (4) where (58) Field of Classification Search .................... 560/51, R" represents a C- alkyl group, arylmethyl group, or substi 560/76, 78, 81, 103, 106, 109, 130, 146, tuted arylmethyl group. 560/174, 176, 190, 191 See application file for complete search history. (4) (56) References Cited U.S. PATENT DOCUMENTS 4,399.287 A 8, 1983 Baillie et al. 6,936,444 B1 8, 2005 BartSch 2008. O146837 A1 6, 2008 Minowa et al. 2009,027O647 A1 10, 2009 Minowa et al. 5 Claims, No Drawings US 8,017,797 B2 1. 2 METHOD FOR PRODUCING byproduct such as chlorine gas is produced, which makes its PHOSPHORUS-CONTAINING O-KETOACD procedural work difficult; and the preparation of methyldi chlorophosphine is difficult and expensive. RELATED APPLICATION It is an object of the present invention to provide a method for producing 4-(hydroxymethylphosphinyl)-2-oxobutanoic The present application is an application claiming the pri acid, which is a production intermediate of L-AMPB which is ority based on Japanese patent application no. 2007-76541, useful as a herbicide, efficiently. filed on Mar. 23, 2007, and the entire disclosure of said Japanese patent application is incorporated herein by refer As a result of considering the reaction of 3-(hydroxymeth ence thereto. 10 ylphosphinyl)-propionic acid ester (-propionate) and Oxalic acid diester in detail, the present inventors found that 4-(hy FIELD OF THE INVENTION droxymethylphosphinyl)-2-oxobutanoic acid can be obtained with improved yield by performing the reaction in a range of The present invention relates to a method for producing reaction temperature between 40-60°C. within a range of 2-3 4-(hydroxymethylphosphinyl)-2-oxobutanoic acid which is 15 equivalents of a used amount of a base followed by acid useful as a production intermediate of a herbicide: L-2- hydrolysis and decarboxylation. Further, it was found that amino-4-(hydroxymethylphosphinyl)-butanoic acid (in the 3-(hydroxymethylphosphinyl)-propionic acid ester as a raw below, it is abbreviated as L-AMPB). material can be produced efficiently from 3-(hydroxymeth ylphosphinyl)-propionic acid ester which is inexpensive, BACKGROUND ART thereby the present invention has been accomplished. It has been hitherto known that 4- (hydroxymethylphos That is to say, the present invention is as follows. phinyl)-oxobutanoic acid is an useful production intermedi In a first aspect of the present invention, there is provided a ate of L-AMPB having herbicidal activity (see patent docu method for producing a compound which is important as a ments 1, 2 and 3; and non-patent document 1). 25 precursor compound and represented by the following for Also, it is only known as a method for synthesizing 4-(hy droxymethylphosphinyl)-oxobutanoic acid that 3-(alkoxym mula (6), ethylphosphinyl)-propionic acid ester (-propionate) or 3-(hy droxymethylphosphinyl)-propionic acid ester and oxalic acid (6) diester are Subjected to condensation reaction, then subjected 30 to hydrolysis and decarboxylation (see patent document 4). In addition, it is known as a method for synthesizing 3-(hy droxymethylphosphinyl)-propionic acid ester that meth ylphosphinic acid is subjected to an addition reaction with acrylic acid ester (acrylate) (see patent document 5 and non 35 patent document 2). On the other hand, 3-(alkoxymeth ylphosphinyl)-propionic acid ester is synthesized Such that in the formula, R' representing C, alkyl group, arylm methyldichlorophosphine is subjected to an addition reaction ethyl group, or substituted arylmethyl group; R represents with acrylic acid, then the produced acid chloride is subjected Calkyl group, arylmethyl group, or substituted arylmethyl to a reaction with alcohol (see non-patent documents 3 and 4). 40 group; Patent document 1: JP Kokai Publication HO1-27485A wherein a compound represented by the following formula Patent document 2: JP Kohyo Publication 2003-528572A (4) is reacted with a compound represented by the following Patent document 3: JP Kokai Publication S59-184196A formula (5) under the existence of a base of 2-3 equivalents Patent document 4: JP Kokai Publication S56-92897A based on the compound of formula (4). Patent document 5: JP Kokai Publication H05-247068A 45 Non-Patent document 1: J. Org. Chem. 56, 1783-1788 (1991) (4) Non-Patent document 2: Angw. Chem. Int. Ed. Engl., 20, 223 (1981) Non-Patent document 3: Zh. Obshch. Khim., 42, 1730(1972) 50 Non-Patent document 4: Zh. Obshch. Khim., 37, 710 (1967) SUMMARY in the formula, R' representing the same meaning as afore mentioned The following analysis is given by the present invention. 55 The above patent documents 1-5 and non-patent documents (COOR.), (5) 1-4 are incorporated herein by references thereto. However, the production yield of 4-(hydroxymethylphos in the formula, R representing the same meaning as afore phinyl)-2-oxobutanoic acid is as low as about 40% in the mentioned. synthesizing method of the patent document 4 using 3-(hy 60 And, in a second aspect of the present invention, there is droxymethylphosphinyl)-propionate ester. provided a method for producing a compound of formula (6), In addition, in the methods of patent document 5 and non as a step for producing the compound of formula (4), com patent document 2, there is a problem that methylphosphinic prising: acid is hard to be prepared and the preparation is expensive. a step that a compound represented by the following for Furthermore, in the methods of non-patent documents 3 65 mula (1) is reacted with a compound represented by the and 4, there are problems such that the addition reaction is a following formula (2) under the existence of an acid or the reaction under high temperature and high pressure, so that existence of a condensation agent and a base, US 8,017,797 B2 4 is reacted with a compound represented by the following (1) formula (2) ROH (2) in the formula, R' representing C, alkyl group, arylm (2) ethyl group, or Substituted arylmethyl group under the exist ence of an acid or the existence of a condensation agent and a base; or the compound of the formula (1) is reacted with a com ROH (2) 10 pound represented by the following formula (3) under the existence of a base in the formula, R' representing the same meaning as defined in the aforementioned formula (6). RX (3) Further, in a third aspect of the present invention, there is in the formula, R' representing the same meaning as afore provided a method for producing a compound of formula (6), mentioned, and X represents halogen atom; or as a step for producing the compound of formula (4), com 15 the compound of the formula (1) is reacted with isobuty prising: lene under the existence of an acid catalyst; to produce a a step that the compound of the formula (1) is reacted with compound represented by the following formula (4), a compound represented by the following formula (3) under the existence of a base, (4) RIX (3) N in the formula, R' representing the same meaning as P defined in the aforementioned formula (6) and X represents Ho1 N1)-coor halogen atom. Also, in a forth aspect of the present invention, there is 25 in the formula, R' representing the same meaning as afore provided a method for producing a compound of formula (6), mentioned, thereafter, as a step for producing the compound of the formula (4), (b) the compound of formula (4) is reacted with a com comprising a step that the compound of the formula (1) is pound represented by the following formula (5) under the reacted with isobutylene under the existence of an acid cata existence of a base of 2-3 equivalents based on the compound lyst.
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