JPH06501925A - アシルアミノメタンホスホン酸およびアシルアミノメタンホスフィン酸の製造方法 - Google Patents
アシルアミノメタンホスホン酸およびアシルアミノメタンホスフィン酸の製造方法Info
- Publication number
- JPH06501925A JPH06501925A JP3513168A JP51316891A JPH06501925A JP H06501925 A JPH06501925 A JP H06501925A JP 3513168 A JP3513168 A JP 3513168A JP 51316891 A JP51316891 A JP 51316891A JP H06501925 A JPH06501925 A JP H06501925A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- acid
- phenyl
- alkyl
- carbon atoms
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 239000002253 acid Substances 0.000 title abstract description 30
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims abstract description 45
- 238000000034 method Methods 0.000 claims abstract description 24
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 14
- 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 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- OHWRASKXEUIFFB-UHFFFAOYSA-N NCP(O)=O Chemical compound NCP(O)=O OHWRASKXEUIFFB-UHFFFAOYSA-N 0.000 claims description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 abstract description 6
- 239000000543 intermediate Substances 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000001816 cooling Methods 0.000 description 13
- 238000010992 reflux Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000003756 stirring Methods 0.000 description 9
- 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
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- UOUBPDZUBVJZOQ-UHFFFAOYSA-N n-(hydroxymethyl)benzamide Chemical compound OCNC(=O)C1=CC=CC=C1 UOUBPDZUBVJZOQ-UHFFFAOYSA-N 0.000 description 5
- 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 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000000052 vinegar Substances 0.000 description 4
- 235000021419 vinegar Nutrition 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical compound NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000000967 suction filtration Methods 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 239000012043 crude product Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 238000002156 mixing Methods 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
- 239000007858 starting material Substances 0.000 description 2
- 238000010626 work up procedure Methods 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
- QLZHNIAADXEJJP-UHFFFAOYSA-N Phenylphosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-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
- 150000001408 amides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- HRQGCQVOJVTVLU-UHFFFAOYSA-N bis(chloromethyl) ether Chemical compound ClCOCCl HRQGCQVOJVTVLU-UHFFFAOYSA-N 0.000 description 1
- 239000003183 carcinogenic agent Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- HKYGSMOFSFOEIP-UHFFFAOYSA-N dichloro(dichloromethoxy)methane Chemical compound ClC(Cl)OC(Cl)Cl HKYGSMOFSFOEIP-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical compound NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 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
- 238000000746 purification Methods 0.000 description 1
- 238000000926 separation method Methods 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)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.式I ▲数式、化学式、表等があります▼(I)〔式中、R1は水酸基、炭素原子数1 〜4のアルキルまたはフェニルでありそしてR2は水素原子、炭素原子数1〜6 のアルキル、ベンジルあるいは、非置換であるかまたは炭素原子数1〜4のアル キル、炭素原子数1〜4のアルコキシおよびハロゲン原子の群の内の一つまたは 複数の残基で置換されているフェニルである。〕 で表される化合物を製造する方法において、式IIR2−CO−NH−CH2− OH(II)〔式中、R2は上述の意味を有する。〕で表される化合物を式II I ▲数式、化学式、表等があります▼(III)〔式中、R1は上述の意味を有す る。〕で表される化合物と、式IIの化合物を基準として少なくとも1当量の無 水酢酸の存在下に反応させることを特徴とする、上記方法。 2.R1が水酸基である請求項1に記載の方法。 3.R1がメチル、エチルまたはフェニルを意味する請求項1に記載の方法。 4.R2が水素原子、炭素原子数1〜3のアルキル、ベンジルまたはフェニルを 意味する請求項1、2または3に記載の方法。 5.R2がフェニルを意味する請求項1、2または3に記載の方法。 6.式IIおよびIIIの化合物および無水酢酸を1:1:1.5〜1:(1〜 1.1):8のモル比で反応させる請求項1〜5の一つまたは複数に記載の方法 。 7.1:1:1.5〜1:1:4のモル比である請求項6に記載の方法。 8.反応の終了後に過剰の無水酢酸を加水分解する請求項6または7に記載の方 法。 9.式IIの化合物とIIIの化合物との反応を有機溶剤の存在下に実施する請 求項1〜7のいずれか一つに記載の方法。 10.溶剤が酢酸である請求項9に記載の方法。 11.式(I) ▲数式、化学式、表等があります▼(I)〔式中、R1は炭素原子数1〜4のア ルキルまたはフェニルでありそしてR2は水素原子、炭素原子数1〜6のアルキ ル、ベンジルあるいは、非置換であるかまたは炭素原子数1〜4のアルキル、炭 素原子数1〜4のアルコキシおよびハロゲン原子の群の内の一つまたは複数の残 基で置換されているフェニルである。〕 で表される化合物。 12.R1がメチル、エチルまたはフェニルでありそしてR2が水素原子、メチ ルまたはフェニルを意味する請求項11に記載の化合物。 13.請求項11または12に記載の化合物を式H2NCH2(O)(R1)( OH)のアミノメチルホスフィン酸の製造に用いる方法。
Applications Claiming Priority (3)
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 |
DE4026026.7 | 1990-08-17 | ||
PCT/EP1991/001495 WO1992003450A1 (de) | 1990-08-17 | 1991-08-07 | Herstellung von acylaminomethanphosphonsäuren und acylaminomethanphosphinsäuren |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH06501925A true JPH06501925A (ja) | 1994-03-03 |
JP3236612B2 JP3236612B2 (ja) | 2001-12-10 |
Family
ID=6412398
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP51316891A Expired - Fee Related JP3236612B2 (ja) | 1990-08-17 | 1991-08-07 | アシルアミノメタンホスホン酸およびアシルアミノメタンホスフィン酸の製造方法 |
Country Status (15)
Country | Link |
---|---|
US (1) | US5432291A (ja) |
EP (1) | EP0543850B1 (ja) |
JP (1) | JP3236612B2 (ja) |
CN (1) | CN1028995C (ja) |
AT (1) | ATE131485T1 (ja) |
AU (1) | AU8310091A (ja) |
CA (1) | CA2089652C (ja) |
DE (2) | DE4026026A1 (ja) |
DK (1) | DK0543850T3 (ja) |
ES (1) | ES2082220T3 (ja) |
IE (1) | IE912919A1 (ja) |
IL (1) | IL99202A (ja) |
PT (1) | PT98699B (ja) |
WO (1) | WO1992003450A1 (ja) |
ZA (1) | ZA916503B (ja) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104812766B (zh) | 2012-07-17 | 2017-06-06 | 斯特雷特马克控股股份公司 | 用于合成氨基亚烷基膦酸的方法 |
US20150232493A1 (en) | 2012-07-17 | 2015-08-20 | Straitmark Holding Ag | Method for the synthesis of alpha-aminoalkylenephosphonic acid |
WO2014012986A1 (en) | 2012-07-17 | 2014-01-23 | Straitmark Holding Ag | Method for the synthesis of n-phosphonomethyliminodiacetic acid |
US9676799B2 (en) | 2012-07-17 | 2017-06-13 | Straitmark Holding Ag | Method for the synthesis of N-(phosphonomethyl)glycine |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 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 ES ES91914144T patent/ES2082220T3/es not_active Expired - Lifetime
- 1991-08-07 EP EP91914144A patent/EP0543850B1/de not_active Expired - Lifetime
- 1991-08-07 CA CA002089652A patent/CA2089652C/en not_active Expired - Fee Related
- 1991-08-07 AT AT91914144T patent/ATE131485T1/de not_active IP Right Cessation
- 1991-08-07 DK DK91914144.0T patent/DK0543850T3/da active
- 1991-08-07 DE DE59107093T patent/DE59107093D1/de not_active Expired - Fee Related
- 1991-08-07 WO PCT/EP1991/001495 patent/WO1992003450A1/de active IP Right Grant
- 1991-08-15 IL IL9920291A patent/IL99202A/en not_active IP Right Cessation
- 1991-08-16 ZA ZA916503A patent/ZA916503B/xx unknown
- 1991-08-16 IE IE291991A patent/IE912919A1/en unknown
- 1991-08-16 CN CN91105717A patent/CN1028995C/zh not_active Expired - Fee Related
- 1991-08-16 PT PT98699A patent/PT98699B/pt not_active IP Right Cessation
-
1993
- 1993-02-11 US US07/969,167 patent/US5432291A/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
CA2089652A1 (en) | 1992-02-18 |
WO1992003450A1 (de) | 1992-03-05 |
ATE131485T1 (de) | 1995-12-15 |
DK0543850T3 (da) | 1996-03-11 |
CN1028995C (zh) | 1995-06-21 |
IE912919A1 (en) | 1992-02-26 |
CN1059147A (zh) | 1992-03-04 |
PT98699A (pt) | 1992-07-31 |
PT98699B (pt) | 1999-01-29 |
IL99202A0 (en) | 1992-07-15 |
DE4026026A1 (de) | 1992-02-20 |
ZA916503B (en) | 1992-04-29 |
DE59107093D1 (de) | 1996-01-25 |
JP3236612B2 (ja) | 2001-12-10 |
CA2089652C (en) | 2001-09-18 |
IL99202A (en) | 1995-10-31 |
AU8310091A (en) | 1992-03-17 |
EP0543850A1 (de) | 1993-06-02 |
EP0543850B1 (de) | 1995-12-13 |
US5432291A (en) | 1995-07-11 |
ES2082220T3 (es) | 1996-03-16 |
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