Title:
PROCESS FOR THE PREPARATION OF N-PHOSPHONO-METHYLGLYCINE AND DERIVATIVES THEREOF
Document Type and Number:
WIPO Patent Application WO2005019230
Kind Code:
A3
Abstract:
N-phosphonomethylamines are produced by reaction of an amine substrate with a halomethylphosphonic acid or salt thereof, a hydroxymethylphosphonic acid or salt thereof, or a dehydrated self-ester dimer, trimer or oligomer of hydroxymethylphosphonic acid. Among the products that may be prepared according to the process are N-phosphonomethylaminocarboxylic acids such as (e.g.) glyphosate, N-phosphonomethylaminoalkanols such as (e.g.) hydroxyethlaminomethylphosphonic acid, and N-acylaminomethylphosphonic acids such as (e.g.) N-carbamylaminomethylphosphonic acid. Certain reactions are conducted with a substantial excess of amine reactant in order to drive the conversion while avoiding excessive formation of bis(N-phosphonomethyl)amine by-products. Other reactions use a secondary amine substrate (such as iminodiacetic acid) and can be conducted at substantial equimolar ratios of halomethylaminomethylphosphonic acid or hydroxyaminomethylphosphonic acid to secondary amine reactant without significant formation of bis(phosphonomethyl)amine by-products. Further disclosed is a process for the preparation of hydroxymethylphosphonic acid self-ester dimers, trimers and oligomers by azeotropic dehydration.
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Inventors:
COLEMAN JAMES P (US)
EBNER JERRY R (US)
HAUPFEAR ERIC A (US)
LENNON PATRICK J (US)
SCHAPER JOSEPH A (US)
TREMONT SAMUEL J (US)
WOLFSON SERGE G (US)
BRODSKY PHILIP H (US)
EBNER JERRY R (US)
HAUPFEAR ERIC A (US)
LENNON PATRICK J (US)
SCHAPER JOSEPH A (US)
TREMONT SAMUEL J (US)
WOLFSON SERGE G (US)
BRODSKY PHILIP H (US)
Application Number:
PCT/US2004/027413
Publication Date:
August 04, 2005
Filing Date:
August 23, 2004
Export Citation:
Assignee:
MONSANTO TECHNOLOGY LLC (US)
COLEMAN JAMES P (US)
EBNER JERRY R (US)
HAUPFEAR ERIC A (US)
LENNON PATRICK J (US)
SCHAPER JOSEPH A (US)
TREMONT SAMUEL J (US)
WOLFSON SERGE G (US)
BRODSKY PHILIP H (US)
COLEMAN JAMES P (US)
EBNER JERRY R (US)
HAUPFEAR ERIC A (US)
LENNON PATRICK J (US)
SCHAPER JOSEPH A (US)
TREMONT SAMUEL J (US)
WOLFSON SERGE G (US)
BRODSKY PHILIP H (US)
International Classes:
C07F9/28; C07F9/38; (IPC1-7): C07F9/38
Foreign References:
| US4661298A | 1987-04-28 | |||
| FR2276312A1 | 1976-01-23 | |||
| US3977860A | 1976-08-31 | |||
| FR2568882A1 | 1986-02-14 | |||
| US2328358A | 1943-08-31 |
Other References:
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LOMBAERT ET AL.: "N-Phosphonomethyl Dipeptides and their Phosphonate Prodrugs, a New Generation of Neutral Endopeptidase (NEP, EC 3.4.24.11) Inhibitors", J. MED. CHEM., vol. 37, 1994, pages 498 - 511, XP002327949
AVILA ET AL.: "Chemical and Mutagenic Analysis of Aminomethylphosphonate Biodegradation", J. AM. CHEM. SOC., vol. 109, no. 22, 1987, pages 6758 - 6764, XP002327950
DU S ET AL: "Synthesis and evaluation of putative oxocarbenium intermediate mimic in the KDO8P synthase-catalyzed reaction as a tool for the design of potent inhibitors for lipopolysaccharide biosynthesis", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, OXFORD, GB, vol. 7, no. 19, 7 October 1997 (1997-10-07), pages 2469 - 2472, XP004136466, ISSN: 0960-894X
WALLACE E M ET AL: "DESIGN AND SYNTHESIS OF POTENT, SELECTIVE INHIBITORS OF ENDOTHELIN-CONVERTING ENZYME", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY. WASHINGTON, US, vol. 41, 1998, pages 1513 - 1523, XP001094342, ISSN: 0022-2623
STORZ ET AL.: "N-Monoalkylation of Tetra-O-benzyl-D-arabinonamide: Synthesis of Some Open-Chain Analogues of N-Acetylneuraminic Acid and Their Evaluation as Sialidase Inhibitors", HELV. CHIM. ACTA, vol. 81, no. 10, 1998, pages 1896 - 1907, XP002327951
CAMERON ET AL.: "Organophosphorous compounds as potential fungicides. Part I.", PHOSPHOROUS AND SULFUR, vol. 40, 1988, pages 183 - 198, XP009047520
MAIER: "Organic phosphorous compounds 98. Synthesis and Porperties of N-methylaminoethylphosphonic acid an derivatives", PHOSPHOROUS, SULFUR, AND SILICON, vol. 62, 1991, pages 29 - 34, XP009047521
HUDSON ET AL.: "An approach to the development of organophosphorous fungicides", PHOSPHOROUS, SULFUR, AND SILICON, vol. 109, 1996, pages 345 - 348, XP009047522
LOMBAERT ET AL.: "N-Phosphonomethyl Dipeptides and their Phosphonate Prodrugs, a New Generation of Neutral Endopeptidase (NEP, EC 3.4.24.11) Inhibitors", J. MED. CHEM., vol. 37, 1994, pages 498 - 511, XP002327949
AVILA ET AL.: "Chemical and Mutagenic Analysis of Aminomethylphosphonate Biodegradation", J. AM. CHEM. SOC., vol. 109, no. 22, 1987, pages 6758 - 6764, XP002327950
DU S ET AL: "Synthesis and evaluation of putative oxocarbenium intermediate mimic in the KDO8P synthase-catalyzed reaction as a tool for the design of potent inhibitors for lipopolysaccharide biosynthesis", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, OXFORD, GB, vol. 7, no. 19, 7 October 1997 (1997-10-07), pages 2469 - 2472, XP004136466, ISSN: 0960-894X
WALLACE E M ET AL: "DESIGN AND SYNTHESIS OF POTENT, SELECTIVE INHIBITORS OF ENDOTHELIN-CONVERTING ENZYME", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY. WASHINGTON, US, vol. 41, 1998, pages 1513 - 1523, XP001094342, ISSN: 0022-2623
STORZ ET AL.: "N-Monoalkylation of Tetra-O-benzyl-D-arabinonamide: Synthesis of Some Open-Chain Analogues of N-Acetylneuraminic Acid and Their Evaluation as Sialidase Inhibitors", HELV. CHIM. ACTA, vol. 81, no. 10, 1998, pages 1896 - 1907, XP002327951
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