ZA200300005B - 4-alkoxy cyclohexane-1 amino carboxylic acid esters and method for the production thereof. - Google Patents
4-alkoxy cyclohexane-1 amino carboxylic acid esters and method for the production thereof. Download PDFInfo
- Publication number
- ZA200300005B ZA200300005B ZA200300005A ZA200300005A ZA200300005B ZA 200300005 B ZA200300005 B ZA 200300005B ZA 200300005 A ZA200300005 A ZA 200300005A ZA 200300005 A ZA200300005 A ZA 200300005A ZA 200300005 B ZA200300005 B ZA 200300005B
- Authority
- ZA
- South Africa
- Prior art keywords
- formula
- compounds
- iii
- defined above
- alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 16
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 47
- -1 alkali metal cyanides Chemical class 0.000 claims description 17
- 229910052783 alkali metal Inorganic materials 0.000 claims description 12
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims description 11
- 235000012501 ammonium carbonate Nutrition 0.000 claims description 11
- 239000001099 ammonium carbonate Substances 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 7
- 150000002576 ketones Chemical class 0.000 description 7
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 6
- 150000001469 hydantoins Chemical class 0.000 description 5
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 5
- 238000006150 Bucherer-Bergs reaction Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 244000309464 bull Species 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- ZRXHLJNBNWVNIM-UHFFFAOYSA-N 3-methyl-1-benzofuran Chemical compound C1=CC=C2C(C)=COC2=C1 ZRXHLJNBNWVNIM-UHFFFAOYSA-N 0.000 description 2
- 238000007059 Strecker synthesis reaction Methods 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XADCKKKOYZJNAR-UHFFFAOYSA-N 4-methoxycyclohexan-1-one Chemical compound COC1CCC(=O)CC1 XADCKKKOYZJNAR-UHFFFAOYSA-N 0.000 description 1
- 241000949477 Toona ciliata Species 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000003997 cyclic ketones Chemical class 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
- 229940091173 hydantoin Drugs 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/46—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C229/48—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups and carboxyl groups bound to carbon atoms of the same non-condensed ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/09—Geometrical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10032587A DE10032587A1 (de) | 2000-07-05 | 2000-07-05 | 4-Alkoxy-cyclohexan-1-amino-carbonsäureester und Verfahren zu ihrer Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200300005B true ZA200300005B (en) | 2004-01-02 |
Family
ID=7647819
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200300005A ZA200300005B (en) | 2000-07-05 | 2003-01-02 | 4-alkoxy cyclohexane-1 amino carboxylic acid esters and method for the production thereof. |
Country Status (16)
| Country | Link |
|---|---|
| US (3) | US7148377B2 (es) |
| EP (1) | EP1309562B1 (es) |
| JP (5) | JP5127106B2 (es) |
| KR (1) | KR100758620B1 (es) |
| CN (2) | CN1183118C (es) |
| AT (1) | ATE394379T1 (es) |
| AU (1) | AU2001272504A1 (es) |
| BR (1) | BR0112245B1 (es) |
| DE (2) | DE10032587A1 (es) |
| DK (1) | DK1309562T3 (es) |
| ES (1) | ES2305090T3 (es) |
| HK (1) | HK1057897A1 (es) |
| IL (3) | IL153561A0 (es) |
| MX (1) | MXPA02012889A (es) |
| WO (1) | WO2002002532A1 (es) |
| ZA (1) | ZA200300005B (es) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10032587A1 (de) * | 2000-07-05 | 2002-01-17 | Bayer Ag | 4-Alkoxy-cyclohexan-1-amino-carbonsäureester und Verfahren zu ihrer Herstellung |
| DE10213051B4 (de) * | 2002-03-23 | 2013-03-07 | Grünenthal GmbH | Substituierte 4-Aminocyclohexanole |
| DE10231333A1 (de) * | 2002-07-11 | 2004-01-22 | Bayer Cropscience Ag | Cis-Alkoxysubstituierte spirocyclische 1-H-Pyrrolidin-2,4-dion-Derivate |
| DE10239479A1 (de) * | 2002-08-28 | 2004-03-04 | Bayer Cropscience Ag | Substituierte spirocyclische Ketoenole |
| DE10241062A1 (de) * | 2002-09-05 | 2003-11-27 | Bosch Gmbh Robert | Strukturkörper mit einem elektrochemisch erzeugten porösen Bereich |
| DE102006057037A1 (de) * | 2006-12-04 | 2008-06-05 | Bayer Cropscience Ag | cis-Alkoxyspirocyclische biphenylsubstituierte Tetramsäure-Derivate |
| DK3372580T3 (da) | 2011-01-25 | 2020-10-12 | Bayer Cropscience Ag | Fremgangsmåde til fremstilling af 1-h-pyrrolidin-2,4-dion-derivater |
| DE102011080405A1 (de) | 2011-08-04 | 2013-02-07 | Bayer Pharma AG | Substituierte 3-(Biphenyl-3-yl)-8,8-difluor-4-hydroxy-1-azaspiro[4.5]dec-3-en-2-one zur Therapie |
| WO2012110519A1 (de) | 2011-02-17 | 2012-08-23 | Bayer Cropscience Ag | Substituierte 3-(biphenyl-3-yl)-8,8-difluor-4-hydroxy-1-azaspiro[4.5]dec-3-en-2-one zur therapie und halogensubstituierte spirocyclische ketoenole |
| JP5974021B2 (ja) * | 2011-03-11 | 2016-08-23 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | シス−アルコキシ置換されたスピロ環状１ｈ−ピロリジン−２，４−ジオン誘導体 |
| DE102011080406A1 (de) | 2011-08-04 | 2013-02-07 | Bayer Pharma AG | Substituierte 3-(Biphenyl-3-yl)-4-hydroxy-8-methoxy-1-azaspiro8[4.5]dec-3-en-2-one |
| TWI579260B (zh) * | 2012-03-28 | 2017-04-21 | 拜耳智慧財產有限公司 | 用於製備順式－烷氧基－取代之螺環狀苯基乙醯基胺基酸酯及順式－烷氧基－取代之螺環狀１ｈ－吡咯啶－２，４－二酮衍生物之方法 |
| CA2931585A1 (en) | 2013-12-23 | 2015-07-02 | Syngenta Participations Ag | Dihydro-hydantoin derivatives with herbicidal activity |
| CN107857722A (zh) * | 2017-11-21 | 2018-03-30 | 河南紫微星化学有限公司 | 一种螺虫乙酯的新型制备方法 |
| CN110128288B (zh) * | 2018-02-02 | 2023-07-28 | 浙江九洲药业股份有限公司 | 一种氨基取代的环戊烷甲酸烷基酯衍生物的制备方法 |
| CN111574389B (zh) * | 2020-05-14 | 2023-08-18 | 河北威远生物化工有限公司 | 1-氨基-4-取代环己基羧酸及其盐的顺式异构体的制备方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5523822B2 (es) * | 1971-12-14 | 1980-06-25 | ||
| AU666040B2 (en) * | 1992-10-28 | 1996-01-25 | Bayer Aktiengesellschaft | Substituted 1-H-3-aryl-pyrrolidine-2,4-dione derivatives |
| DE4425617A1 (de) * | 1994-01-28 | 1995-08-03 | Bayer Ag | 1-H-3-Aryl-pyrrolidin-2,4-dion-Derivate |
| DE4431730A1 (de) * | 1994-02-09 | 1995-08-10 | Bayer Ag | Substituierte 1H-3-Aryl-pyrrolidin-2,4-dion-Derivate |
| WO1995026954A1 (de) * | 1994-04-05 | 1995-10-12 | Bayer Aktiengesellschaft | Alkoxy-alkyl-substituierte 1-h-3-aryl-pyrrolidin-2,4-dione als herbizide und pestizide |
| MX9706080A (es) * | 1995-02-13 | 1997-10-31 | Bayer Ag | 1,3-cetoenoles heterociclicos 2-fenil-sustituidos como herbicidas pesticidas. |
| CN1221514C (zh) * | 1995-05-09 | 2005-10-05 | 拜尔公司 | 制备烷基－二卤代苯基取代的酮烯醇的中间体 |
| BR9609250B1 (pt) * | 1995-06-28 | 2011-08-23 | 2,4,5-fenilcetoenóis trissubstituìdos, processo para sua preparação, composições para controle de pestes e herbicidas, uso das referidas composições e método para controle de pestes. | |
| DE59610095D1 (de) * | 1995-06-30 | 2003-03-06 | Bayer Cropscience Ag | Dialkyl-halogenphenylsubstituierte ketoenole zur verwendung als herbizide und pestizide |
| US5808146A (en) * | 1995-11-09 | 1998-09-15 | Emory University | Amino acid analogs for tumor imaging |
| DE59712592D1 (de) * | 1996-04-02 | 2006-05-04 | Bayer Cropscience Ag | Substituierte phenylketoenole als schädlingsbekämpfungsmittel und herbizide |
| EP0915846B1 (de) * | 1996-08-05 | 2003-04-23 | Bayer CropScience AG | 2- und 2,5-substituierte phenylketoenole |
| AUPO727097A0 (en) * | 1997-06-10 | 1997-07-03 | Unisearch Limited | Method of treatment of hepatoma and pharmaceutical compositions for use therein |
| DE10032587A1 (de) * | 2000-07-05 | 2002-01-17 | Bayer Ag | 4-Alkoxy-cyclohexan-1-amino-carbonsäureester und Verfahren zu ihrer Herstellung |
| US6380426B1 (en) * | 2001-09-26 | 2002-04-30 | Council Of Scientific And Industrial Research | Process for the preparation of a carboxylic acid |
-
2000
- 2000-07-05 DE DE10032587A patent/DE10032587A1/de not_active Withdrawn
-
2001
- 2001-06-22 JP JP2002507789A patent/JP5127106B2/ja not_active Expired - Lifetime
- 2001-06-22 CN CNB018110401A patent/CN1183118C/zh not_active Expired - Lifetime
- 2001-06-22 AU AU2001272504A patent/AU2001272504A1/en not_active Abandoned
- 2001-06-22 EP EP01951627A patent/EP1309562B1/de not_active Expired - Lifetime
- 2001-06-22 DE DE50113943T patent/DE50113943D1/de not_active Expired - Lifetime
- 2001-06-22 CN CNB2004100789269A patent/CN1286820C/zh not_active Expired - Lifetime
- 2001-06-22 IL IL15356101A patent/IL153561A0/xx active IP Right Grant
- 2001-06-22 ES ES01951627T patent/ES2305090T3/es not_active Expired - Lifetime
- 2001-06-22 DK DK01951627T patent/DK1309562T3/da active
- 2001-06-22 MX MXPA02012889A patent/MXPA02012889A/es active IP Right Grant
- 2001-06-22 WO PCT/EP2001/007115 patent/WO2002002532A1/de active IP Right Grant
- 2001-06-22 KR KR1020027017196A patent/KR100758620B1/ko active IP Right Grant
- 2001-06-22 US US10/332,209 patent/US7148377B2/en not_active Expired - Lifetime
- 2001-06-22 AT AT01951627T patent/ATE394379T1/de active
- 2001-06-22 BR BRPI0112245-2B1A patent/BR0112245B1/pt active IP Right Grant
-
2002
- 2002-12-19 IL IL153561A patent/IL153561A/en unknown
-
2003
- 2003-01-02 ZA ZA200300005A patent/ZA200300005B/en unknown
-
2004
- 2004-02-05 HK HK04100750A patent/HK1057897A1/xx not_active IP Right Cessation
-
2006
- 2006-10-30 US US11/589,366 patent/US7511153B2/en not_active Expired - Lifetime
-
2008
- 2008-04-16 IL IL190905A patent/IL190905A/en active IP Right Grant
-
2009
- 2009-02-19 US US12/388,929 patent/US7803967B2/en not_active Expired - Fee Related
-
2012
- 2012-03-14 JP JP2012057090A patent/JP5805561B2/ja not_active Expired - Lifetime
- 2012-09-14 JP JP2012202818A patent/JP5899092B2/ja not_active Expired - Lifetime
- 2012-09-14 JP JP2012202817A patent/JP5899091B2/ja not_active Expired - Lifetime
-
2014
- 2014-05-14 JP JP2014100409A patent/JP2014167018A/ja active Pending
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