KR860001085A - 티아졸릴프로펜디카르복실산 반 에스테르류의 제조방법 - Google Patents
티아졸릴프로펜디카르복실산 반 에스테르류의 제조방법 Download PDFInfo
- Publication number
- KR860001085A KR860001085A KR1019850004645A KR850004645A KR860001085A KR 860001085 A KR860001085 A KR 860001085A KR 1019850004645 A KR1019850004645 A KR 1019850004645A KR 850004645 A KR850004645 A KR 850004645A KR 860001085 A KR860001085 A KR 860001085A
- Authority
- KR
- South Korea
- Prior art keywords
- thiazolyl
- amino
- protected amino
- propene
- acid ester
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims 6
- 150000002148 esters Chemical class 0.000 title claims 5
- 238000004519 manufacturing process Methods 0.000 title claims 3
- -1 2- (2-amino-4-thiazolyl) malonic acid ester Chemical class 0.000 claims 6
- 238000000034 method Methods 0.000 claims 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical class OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 150000007513 acids Chemical class 0.000 claims 2
- 150000001733 carboxylic acid esters Chemical class 0.000 claims 2
- XVOUMQNXTGKGMA-UHFFFAOYSA-N glutaconic acid Chemical compound OC(=O)CC=CC(O)=O XVOUMQNXTGKGMA-UHFFFAOYSA-N 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims 2
- VCVXTGHARNCYNB-UHFFFAOYSA-N 2-[2-amino-1-(1,3-thiazol-2-yl)ethylidene]propanedioic acid Chemical class OC(=O)C(C(O)=O)=C(CN)C1=NC=CS1 VCVXTGHARNCYNB-UHFFFAOYSA-N 0.000 claims 1
- 239000002841 Lewis acid Substances 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 125000005236 alkanoylamino group Chemical group 0.000 claims 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 235000019445 benzyl alcohol Nutrition 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 150000005826 halohydrocarbons Chemical class 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 150000007517 lewis acids Chemical class 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/40—Unsubstituted amino or imino radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/48—Acylated amino or imino radicals by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof, e.g. carbonylguanidines
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (7)
1) 할로아세틸말론산 에스테르(I)을 티오우레아와 반응시켜 2-(2-아미노-4-티아졸릴)말론산 에스테르(Ⅱ)를 수득하고, 2) 후자의 아미노기를 보호하여 2-(2-보호된 아미노-4-티아졸릴)말론산 에스테르(Ⅲ)을 수득하고, 3) 생성물을 할로알켄산 에스테르로 처리하여 1-(2-보호된 아미노-4-티아졸릴)-2-프로펜-(1,1,3-트리 또는 1,1,3,3-테트라) 카르복실산 에스테르(Ⅳ)를 수득하고, 4) 후자를 가수분해 및 탈카르복실화하여 1-(2-보호된 아미노-4-티아졸릴) 프로펜-1,3-디카르복실산(Ⅴ)를 수득하고 및 5) 생성물을 알코올 및 헤미-에스테르화제와 반응시켜 1-(2-보호된 아미노-4-티아졸릴) 프로펜-1,3-디카르복실산 반 에스테르(Ⅵ)을 수득함을 특징으로 하는 아미노티아졸릴프로펜디카르복실산 유도체류을 제조방법.
(및 이중결합 위치의 이성질체)
(상기 식중, Hal은 할로겐이고; R는 같거나 서로 다른 에스테르-형성기이고; R1및 R2는 각각 수소 또는 아미노-보호기이고; R3는 수소 또는 COOR기이다)
1-(2-보호된 아미노-4-티아졸릴)프로펜-1,3-디카르복실산을 알코올 및 헤미-에스테르화제로 처리함을 특징으로 하는 1-(2-보호된 아미노-4-티아졸릴) 프로펜-1,3-디카르복실산 반 에스테르류의 제조방법.
제2항에 있어서, 알코올이 (1C~5C) 알카놀, (1C~5C) 치환된 알카놀, (2C~8C) 알케놀, 벤질알코올, 또는 (8C~15C) 치환된 벤질 알코올인 방법.
제2항에 있어서, 보호된 아미노가 (1C~5C) 알카노일아미노, (1C~5C) 할로아카노일아미노, (1C~5C) 알콕시카르보닐아미노, (8C~15C) 아르알콕시카르보닐아미노, (13C~20C) 폴리아릴메틸아미노, (1C~15C) 엔아미노, 또는 트리-(1C~5C) 알킬실리아미노인 방법.
제2항에 있어서, 헤미-에스테르화제가 무기산, 알칸설폰산, 아릴설폰산, 루이산, 또는 포스포러스펜톡시드로 부터 선택된 산인 방법.
제2항에 있어서, 반응을 탄화수소, 할로탄화수소, 시약알코올 및 이들의 혼합물로 부터 선택된 용매내에서 수행하는 방법.
제2항에 있어서, 반응을 0~40℃에서 1~200시간 동안 수행하는 방법.
※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14579484A JPS6124580A (ja) | 1984-07-12 | 1984-07-12 | アミノチアゾリルグルタル酸誘導体の製造方法 |
| JP145794-84 | 1984-07-12 | ||
| JP145794 | 1986-06-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR860001085A true KR860001085A (ko) | 1986-02-22 |
| KR920003197B1 KR920003197B1 (ko) | 1992-04-24 |
Family
ID=15393306
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019850004645A KR920003197B1 (ko) | 1984-07-12 | 1985-06-28 | 티아졸릴프로펜디카르복실산 반 에스테르류의 제조방법 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4652652A (ko) |
| EP (1) | EP0168025B1 (ko) |
| JP (1) | JPS6124580A (ko) |
| KR (1) | KR920003197B1 (ko) |
| DE (1) | DE3573252D1 (ko) |
| ES (1) | ES545068A0 (ko) |
| GB (1) | GB2162514B (ko) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6153272A (ja) * | 1984-08-24 | 1986-03-17 | Shionogi & Co Ltd | グルタル酸誘導体の製法 |
| DE3807232A1 (de) * | 1988-03-05 | 1989-09-14 | Bayer Ag | Substituierte acrylsaeureester |
| GB0922204D0 (en) * | 2009-12-18 | 2010-02-03 | Givaudan Sa | Organic Compounds |
| CN111116508A (zh) * | 2019-12-31 | 2020-05-08 | 烟台坤益液晶显示材料有限公司 | 一种头孢布烯7β位侧链中间体合成方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4298375A (en) * | 1979-10-01 | 1981-11-03 | Monsanto Company | 2-Substituted-5-phenyl-4-thiazolecarboxylic acids and their derivatives as safening agents |
| DE3145727A1 (de) * | 1981-11-19 | 1983-05-26 | Bayer Ag, 5090 Leverkusen | Zwischenprodukte, verfahren zu deren herstellung und verfahren zur herstellung von cephalosporinen |
| US4426528A (en) * | 1982-04-01 | 1984-01-17 | Eli Lilly And Company | Purification of syn-(2-aminothiazol-4-yl)methoxyimino)acetic acid |
| AU575854B2 (en) * | 1983-10-04 | 1988-08-11 | Shionogi & Co., Ltd. | 7beta-(carboxyalkenamido) cephalosporins |
| JPS6153272A (ja) * | 1984-08-24 | 1986-03-17 | Shionogi & Co Ltd | グルタル酸誘導体の製法 |
-
1984
- 1984-07-12 JP JP14579484A patent/JPS6124580A/ja active Granted
-
1985
- 1985-06-19 US US06/746,564 patent/US4652652A/en not_active Expired - Lifetime
- 1985-06-20 GB GB08515640A patent/GB2162514B/en not_active Expired
- 1985-06-28 KR KR1019850004645A patent/KR920003197B1/ko not_active IP Right Cessation
- 1985-07-09 EP EP85108491A patent/EP0168025B1/en not_active Expired
- 1985-07-09 DE DE8585108491T patent/DE3573252D1/de not_active Expired
- 1985-07-11 ES ES545068A patent/ES545068A0/es active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| ES8603849A1 (es) | 1986-01-01 |
| US4652652A (en) | 1987-03-24 |
| EP0168025B1 (en) | 1989-09-27 |
| DE3573252D1 (en) | 1989-11-02 |
| KR920003197B1 (ko) | 1992-04-24 |
| EP0168025A1 (en) | 1986-01-15 |
| JPS6124580A (ja) | 1986-02-03 |
| ES545068A0 (es) | 1986-01-01 |
| GB8515640D0 (en) | 1985-07-24 |
| GB2162514B (en) | 1988-04-20 |
| JPH0587512B2 (ko) | 1993-12-16 |
| GB2162514A (en) | 1986-02-05 |
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| FPAY | Annual fee payment |
Payment date: 20050408 Year of fee payment: 14 |
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