IL99202A - Methylphosphinic acylamino acids, a process for their preparation and some new phospholyl acylaminomethyl acids - Google Patents

Methylphosphinic acylamino acids, a process for their preparation and some new phospholyl acylaminomethyl acids

Info

Publication number: IL99202A
Authority: IL; Israel
Prior art keywords: formula; phenyl; alkyl; compounds; acids
Prior art date: 1990-08-17

Application number

IL9920291A

Other languages

English (en)

Hebrew (he)

Other versions

IL99202A0 (en

Original Assignee

Hoechst Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1990-08-17

Filing date

1991-08-15

Publication date

1995-10-31

1991-08-15 Application filed by Hoechst Ag filed Critical Hoechst Ag

1992-07-15 Publication of IL99202A0 publication Critical patent/IL99202A0/xx

1995-10-31 Publication of IL99202A publication Critical patent/IL99202A/en

Links

238000000034 method Methods 0.000 title claims abstract description 29
238000002360 preparation method Methods 0.000 title claims abstract description 10
239000002253 acid Substances 0.000 title abstract description 19
150000007513 acids Chemical class 0.000 title abstract description 14
ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 title 1
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims abstract description 51
150000001875 compounds Chemical class 0.000 claims abstract description 22
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 5
229910052736 halogen Inorganic materials 0.000 claims abstract description 4
150000002367 halogens Chemical class 0.000 claims abstract description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 35
238000006243 chemical reaction Methods 0.000 claims description 9
239000003960 organic solvent Substances 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
OHWRASKXEUIFFB-UHFFFAOYSA-N NCP(O)=O Chemical class NCP(O)=O OHWRASKXEUIFFB-UHFFFAOYSA-N 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
239000000543 intermediate Substances 0.000 abstract description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
239000000203 mixture Substances 0.000 description 20
238000001816 cooling Methods 0.000 description 17
238000003756 stirring Methods 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
UOUBPDZUBVJZOQ-UHFFFAOYSA-N n-(hydroxymethyl)benzamide Chemical compound OCNC(=O)C1=CC=CC=C1 UOUBPDZUBVJZOQ-UHFFFAOYSA-N 0.000 description 6
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
229910052698 phosphorus Inorganic materials 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
239000006227 byproduct Substances 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
HKYGSMOFSFOEIP-UHFFFAOYSA-N dichloro(dichloromethoxy)methane Chemical compound ClC(Cl)OC(Cl)Cl HKYGSMOFSFOEIP-UHFFFAOYSA-N 0.000 description 4
XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical class NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
238000010992 reflux Methods 0.000 description 4
ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
FDNUAHPLMXZWLS-UHFFFAOYSA-N (acetamidomethyl)phosphonic acid Chemical compound CC(=O)NCP(O)(O)=O FDNUAHPLMXZWLS-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
LFSFPNIUQADDIM-UHFFFAOYSA-N benzamidomethylphosphonic acid Chemical compound OP(O)(=O)CNC(=O)C1=CC=CC=C1 LFSFPNIUQADDIM-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
KNQVWTDLQQGKSV-UHFFFAOYSA-O hydroxy-oxo-phenylphosphanium Chemical compound O[P+](=O)C1=CC=CC=C1 KNQVWTDLQQGKSV-UHFFFAOYSA-O 0.000 description 2
HWJHZLJIIWOTGZ-UHFFFAOYSA-N n-(hydroxymethyl)acetamide Chemical compound CC(=O)NCO HWJHZLJIIWOTGZ-UHFFFAOYSA-N 0.000 description 2
239000000376 reactant Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000007787 solid Substances 0.000 description 2
MGRVRXRGTBOSHW-UHFFFAOYSA-N (aminomethyl)phosphonic acid Chemical compound NCP(O)(O)=O MGRVRXRGTBOSHW-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
DFZNUSYMRMOKBK-UHFFFAOYSA-N C.OPO Chemical compound C.OPO DFZNUSYMRMOKBK-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
NTYBHEKOVMEONU-UHFFFAOYSA-N benzamidomethyl(methyl)phosphinic acid Chemical compound CP(O)(=O)CNC(=O)C1=CC=CC=C1 NTYBHEKOVMEONU-UHFFFAOYSA-N 0.000 description 1
BBPSHEVQDYJYJA-UHFFFAOYSA-N benzamidomethyl(phenyl)phosphinic acid Chemical compound C=1C=CC=CC=1P(=O)(O)CNC(=O)C1=CC=CC=C1 BBPSHEVQDYJYJA-UHFFFAOYSA-N 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
230000000711 cancerogenic effect Effects 0.000 description 1
231100000315 carcinogenic Toxicity 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
-1 for example Substances 0.000 description 1
XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 1
229960004592 isopropanol Drugs 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
PMVVRSKJCGEFIY-UHFFFAOYSA-N methylphosphonous acid Chemical compound CP(O)O PMVVRSKJCGEFIY-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
MNQOPPDTVHYCEZ-UHFFFAOYSA-N n-(hydroxymethyl)formamide Chemical compound OCNC=O MNQOPPDTVHYCEZ-UHFFFAOYSA-N 0.000 description 1
150000003009 phosphonic acids Chemical class 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
238000001394 phosphorus-31 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/301—Acyclic saturated acids which can have further substituents on alkyl
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

IL9920291A 1990-08-17 1991-08-15 Methylphosphinic acylamino acids, a process for their preparation and some new phospholyl acylaminomethyl acids IL99202A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE4026026A DE4026026A1 (de)	1990-08-17	1990-08-17	Acylaminomethyl-phosphinsaeuren und verfahren zur herstellung von acylaminomethanphosphonsaeuren und acylaminomethyl-phosphinsaeuren

Publications (2)

Publication Number	Publication Date
IL99202A0 IL99202A0 (en)	1992-07-15
IL99202A true IL99202A (en)	1995-10-31

Family

ID=6412398

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9920291A IL99202A (en)	1990-08-17	1991-08-15	Methylphosphinic acylamino acids, a process for their preparation and some new phospholyl acylaminomethyl acids

Country Status (15)

Country	Link
US (1)	US5432291A (fr)
EP (1)	EP0543850B1 (fr)
JP (1)	JP3236612B2 (fr)
CN (1)	CN1028995C (fr)
AT (1)	ATE131485T1 (fr)
AU (1)	AU8310091A (fr)
CA (1)	CA2089652C (fr)
DE (2)	DE4026026A1 (fr)
DK (1)	DK0543850T3 (fr)
ES (1)	ES2082220T3 (fr)
IE (1)	IE912919A1 (fr)
IL (1)	IL99202A (fr)
PT (1)	PT98699B (fr)
WO (1)	WO1992003450A1 (fr)
ZA (1)	ZA916503B (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DK0639979T3 (da) *	1992-04-23	2002-12-02	Sloan Kettering Inst Cancer	Ligand for c-kit-receptoren og fremgangsmåde til anvendelse heraf
EP0984510B1 (fr)	1998-03-19	2006-06-14	Matsushita Electric Industrial Co., Ltd.	Dispositif d'antenne et unite de communication mobile
EP2875036A1 (fr)	2012-07-17	2015-05-27	Straitmark Holding AG	Procédé de synthèse d'acide aminoalkylènephosphonique
BR112015000995B1 (pt)	2012-07-17	2020-04-28	Monsanto Technology Llc	método para a síntese de n-(fosfonometil)glicina ou um de seus derivados selecionados a partir do grupo que consiste em seus sais, seus ésteres de fosfonato e seus sais de éster de fosfonato
RU2674022C9 (ru)	2012-07-17	2019-01-24	МОНСАНТО ТЕКНОЛОДЖИ ЭлЭлСи	Способ синтеза альфа-аминоалкиленфосфоновой кислоты
RU2015103314A (ru)	2012-07-17	2016-09-10	Страйтмарк Холдинг Аг	Способ синтеза N-фосфонометилиминодиуксусной кислоты

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2328358A (en)	1941-01-23	1943-08-31	Du Pont	Organic compound and process for preparing the same
DE3824961A1 (de)	1988-07-22	1990-01-25	Basf Ag	Verfahren zur herstellung von bis(aminomethyl)-phosphinsaeure oder deren sauren oder basischen salzen
HU203360B (en) *	1988-11-25	1991-07-29	Monsanto Co	Process for producing n-acylamino methylphosphonates

1990
- 1990-08-17 DE DE4026026A patent/DE4026026A1/de not_active Withdrawn
1991
- 1991-08-07 DK DK91914144.0T patent/DK0543850T3/da active
- 1991-08-07 WO PCT/EP1991/001495 patent/WO1992003450A1/fr not_active Ceased
- 1991-08-07 JP JP51316891A patent/JP3236612B2/ja not_active Expired - Fee Related
- 1991-08-07 AU AU83100/91A patent/AU8310091A/en not_active Abandoned
- 1991-08-07 DE DE59107093T patent/DE59107093D1/de not_active Expired - Fee Related
- 1991-08-07 AT AT91914144T patent/ATE131485T1/de not_active IP Right Cessation
- 1991-08-07 CA CA002089652A patent/CA2089652C/fr not_active Expired - Fee Related
- 1991-08-07 EP EP91914144A patent/EP0543850B1/fr not_active Expired - Lifetime
- 1991-08-07 ES ES91914144T patent/ES2082220T3/es not_active Expired - Lifetime
- 1991-08-15 IL IL9920291A patent/IL99202A/en not_active IP Right Cessation
- 1991-08-16 IE IE291991A patent/IE912919A1/en unknown
- 1991-08-16 PT PT98699A patent/PT98699B/pt not_active IP Right Cessation
- 1991-08-16 CN CN91105717A patent/CN1028995C/zh not_active Expired - Fee Related
- 1991-08-16 ZA ZA916503A patent/ZA916503B/xx unknown
1993
- 1993-02-11 US US07/969,167 patent/US5432291A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
CA2089652C (fr)	2001-09-18
CN1059147A (zh)	1992-03-04
PT98699A (pt)	1992-07-31
ATE131485T1 (de)	1995-12-15
PT98699B (pt)	1999-01-29
DK0543850T3 (da)	1996-03-11
DE4026026A1 (de)	1992-02-20
AU8310091A (en)	1992-03-17
EP0543850A1 (fr)	1993-06-02
ES2082220T3 (es)	1996-03-16
IE912919A1 (en)	1992-02-26
JP3236612B2 (ja)	2001-12-10
ZA916503B (en)	1992-04-29
JPH06501925A (ja)	1994-03-03
WO1992003450A1 (fr)	1992-03-05
EP0543850B1 (fr)	1995-12-13
IL99202A0 (en)	1992-07-15
CN1028995C (zh)	1995-06-21
CA2089652A1 (fr)	1992-02-18
US5432291A (en)	1995-07-11
DE59107093D1 (de)	1996-01-25

Legal Events

Date	Code	Title
1996-03-31	FF	Patent granted
1998-02-08	KB	Patent renewed
2001-10-31	KB	Patent renewed
2005-11-20	KB	Patent renewed
2010-10-31	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
KR20010023069A (ko)	2001-03-26	글루포시네이트의 제조방법 및 이를 위한 중간 생성물
US4443609A (en)	1984-04-17	Tetrahydrothiazole phosphonic acids or esters thereof
US4510102A (en)	1985-04-09	Phosphinic acid esters and process for preparing the same
EP0221043B1 (fr)	1991-09-11	Procédé de préparation d'acides aminométhylphosphoniques
US5734072A (en)	1998-03-31	Process for preparing monoalkyl phosphonites
US5432291A (en)	1995-07-11	Preparation of acylaminomethanephosphonic acids and acylaminomethanephosphinic acids
KR870001334B1 (ko)	1987-07-18	N-포스포노 메틸글리신의 제조방법
US5679842A (en)	1997-10-21	Process for the preparation of aminomethanephosphonic acid and aminomethylphosphinic acids
KR930002412B1 (ko)	1993-03-30	N-아실-아미노메틸 포스포네이트의 제조방법
US5155257A (en)	1992-10-13	Process for the preparation of acylaminomethanephosphonic acids
CS240964B2 (en)	1986-03-13	Preparation method of n-phosphonomethylglycine
JP3111076B2 (ja)	2000-11-20	アミノメタンホスホン酸およびアミノメチル―ホスフィン酸の製造方法
IE912921A1 (en)	1992-02-26	Process for the preparation of aminomethylphosphonic acid¹and aminomethylphosphinic acids from N-hydroxymethylamides
US4368162A (en)	1983-01-11	Process for producing aminomethylphosphonic acid
US5041627A (en)	1991-08-20	Preparation of N-acyl-aminomethylphosphonates
EP0107464B1 (fr)	1986-01-08	Procédé de préparation de la N-phosphonométhylglycine
US4569802A (en)	1986-02-11	Method for preparation of N-phosphonomethylglycine
SU1754720A1 (ru)	1992-08-15	Способ получени эфиров 3-(0,0-диалкилфосфорил)пропановых кислот
SU1735299A1 (ru)	1992-05-23	Способ получени S-триалкилстанниловых эфиров 0,0-диалкилдитиофосфорных кислот
US4524211A (en)	1985-06-18	Process for the production of substituted phosphonic and phosphinic acids and thiazolidinyl phosphonic and phosphinic acid ester intermediates