KR100357651B1 - 시킴산 및 그의 염의 제조방법 - Google Patents
시킴산 및 그의 염의 제조방법 Download PDFInfo
- Publication number
- KR100357651B1 KR100357651B1 KR1019990016579A KR19990016579A KR100357651B1 KR 100357651 B1 KR100357651 B1 KR 100357651B1 KR 1019990016579 A KR1019990016579 A KR 1019990016579A KR 19990016579 A KR19990016579 A KR 19990016579A KR 100357651 B1 KR100357651 B1 KR 100357651B1
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- group
- protecting group
- hydrogen
- compound
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C62/30—Unsaturated compounds
- C07C62/32—Unsaturated compounds containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/317—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
- C07C67/327—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by elimination of functional groups containing oxygen only in singly bound form
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (11)
- 삭제
- 하기 화학식 1의 화합물 또는 그의 염을 실온 내지 100℃의 온도하에 극성 비양자성 용매 속에서 빌스마이어 시약(Vilsmeier reagent)으로 탈수시켜 시킴산(shikimic acid) 또는 그의 염을 생성하는 것을 특징으로 하는 시킴산 또는 그의 염의 제조방법:화학식 1상기 식에서,R1은 수소 또는 카복실산 보호기이고,R2는 수소 또는 하이드록시 보호기이고,R3은 수소 또는 하이드록시 보호기이거나,R2와 R3은 함께 1,2-디올 보호기를 형성하고,R4는 수소 또는 하이드록시 보호기이다.
- 제 2항에 있어서,R1이 수소 또는 알킬인 화학식 1의 화합물을 탈수시키는 것을 특징으로 하는 방법.
- 제 2항에 있어서,R2, R3및 R4가 수소인 화학식 1의 화합물을 탈수시키는 것을 특징으로 하는 방법.
- 제 2항에 있어서,R2, R3및 R4중 하나 이상이 하이드록시 보호기인 화학식 1의 화합물을 탈수시키는 것을 특징으로 하는 방법.
- 제 5항에 있어서,보호기 또는 보호기들이 아실기, 알킬기, 또는 아실기 및 알킬기인 것을 특징으로 하는 방법.
- 제 5항에 있어서,R2와 R3이 함께 알킬리덴기를 나타내고 R4가 아실기인 것을 특징으로 하는 방법.
- 제 7항에 있어서,R4가 설폰산 잔기인 것을 특징으로 하는 방법.
- 제 2항에 있어서,화학식 1의 화합물이 3,4-이소프로필리덴-5-메실-퀸산 에틸 에스테르인 것을 특징으로 하는 방법.
- 제 2항에 있어서,에틸 아세테이트중에서 빌스마이어 시약과 반응시키는 것을 특징으로 하는 방법.
- 제 2항에 있어서,디메틸포름아미드중에서 POCl3, 옥살릴 디클로라이드 또는 포스겐을 사용하여 동일한 반응계에서 빌스마이어 시약을 형성시키는 것을 특징으로 하는 방법.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP98108655 | 1998-05-13 | ||
EP98108655.6 | 1998-05-13 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR19990088155A KR19990088155A (ko) | 1999-12-27 |
KR100357651B1 true KR100357651B1 (ko) | 2002-10-25 |
Family
ID=8231920
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019990016579A KR100357651B1 (ko) | 1998-05-13 | 1999-05-10 | 시킴산 및 그의 염의 제조방법 |
Country Status (10)
Country | Link |
---|---|
US (1) | US6130354A (ko) |
EP (1) | EP0957078B1 (ko) |
JP (1) | JP3641384B2 (ko) |
KR (1) | KR100357651B1 (ko) |
CN (1) | CN1075485C (ko) |
AT (1) | ATE209621T1 (ko) |
CA (1) | CA2271396C (ko) |
DE (1) | DE69900483T2 (ko) |
DK (1) | DK0957078T3 (ko) |
ES (1) | ES2167975T3 (ko) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20240079156A (ko) | 2022-11-28 | 2024-06-04 | 주식회사 엠퍼플 | 침엽수를 이용한 시킴산 추출 방법 |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6518438B2 (en) | 1996-08-23 | 2003-02-11 | Gilead Sciences, Inc. | Preparation of cyclohexene carboxylate derivatives |
CN100386301C (zh) * | 2006-04-12 | 2008-05-07 | 刘润民 | 一种莽草酸生产方法 |
CN101230001B (zh) * | 2007-12-13 | 2012-03-21 | 无锡宏瑞生物医药科技有限公司 | 3-位酰化莽草酸或莽草酸甲(乙)酯衍生物 |
CN102099956B (zh) * | 2008-07-15 | 2013-08-28 | 宇部兴产株式会社 | 锂电池用非水电解液、使用其的锂电池以及用于该锂电池的含有甲酰氧基的化合物 |
KR20140077901A (ko) | 2011-09-07 | 2014-06-24 | 신슈 다이가쿠 | 사상균으로부터 유용 대사 산물을 생산하는 방법 |
CN102633629B (zh) * | 2012-04-01 | 2013-11-27 | 浙江师范大学 | 一种莽草酸的合成方法 |
WO2014208753A1 (ja) * | 2013-06-28 | 2014-12-31 | 富士フイルム株式会社 | シキミ酸誘導体の製造法および中間体 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE759917T1 (de) * | 1995-02-27 | 1998-10-22 | Gilead Sciences Inc | Neue selektive inhibitoren viraler oder bakterieller neuraminidasen |
EP0968994B1 (en) * | 1996-08-19 | 2002-11-06 | Ube Industries, Ltd. | Process for producing substituted trifluorobenzoic acids and esters thereof |
EP0920410B1 (en) * | 1996-08-23 | 2002-03-27 | Gilead Sciences, Inc. | Preparation of cyclohexene carboxylate derivatives |
JPH1121267A (ja) * | 1997-06-30 | 1999-01-26 | Mitsui Chem Inc | (−)−シキミ酸又はその前駆体の製造方法 |
-
1999
- 1999-05-06 AT AT99109014T patent/ATE209621T1/de active
- 1999-05-06 DE DE69900483T patent/DE69900483T2/de not_active Expired - Lifetime
- 1999-05-06 EP EP99109014A patent/EP0957078B1/en not_active Expired - Lifetime
- 1999-05-06 ES ES99109014T patent/ES2167975T3/es not_active Expired - Lifetime
- 1999-05-06 DK DK99109014T patent/DK0957078T3/da active
- 1999-05-07 CA CA002271396A patent/CA2271396C/en not_active Expired - Lifetime
- 1999-05-10 JP JP12792099A patent/JP3641384B2/ja not_active Expired - Lifetime
- 1999-05-10 US US09/307,684 patent/US6130354A/en not_active Expired - Lifetime
- 1999-05-10 KR KR1019990016579A patent/KR100357651B1/ko not_active IP Right Cessation
- 1999-05-13 CN CN99106395A patent/CN1075485C/zh not_active Expired - Lifetime
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20240079156A (ko) | 2022-11-28 | 2024-06-04 | 주식회사 엠퍼플 | 침엽수를 이용한 시킴산 추출 방법 |
Also Published As
Publication number | Publication date |
---|---|
EP0957078B1 (en) | 2001-11-28 |
CN1075485C (zh) | 2001-11-28 |
CN1235151A (zh) | 1999-11-17 |
ES2167975T3 (es) | 2002-05-16 |
DK0957078T3 (da) | 2002-04-02 |
DE69900483T2 (de) | 2002-06-27 |
DE69900483D1 (de) | 2002-01-10 |
CA2271396A1 (en) | 1999-11-13 |
ATE209621T1 (de) | 2001-12-15 |
KR19990088155A (ko) | 1999-12-27 |
US6130354A (en) | 2000-10-10 |
CA2271396C (en) | 2002-10-08 |
JP3641384B2 (ja) | 2005-04-20 |
EP0957078A1 (en) | 1999-11-17 |
JP2000026365A (ja) | 2000-01-25 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP4806351B2 (ja) | スチルベン誘導体を製造する方法 | |
EP3712130B1 (en) | Method for synthesis of roxadustat and intermediate compounds thereof | |
KR100357651B1 (ko) | 시킴산 및 그의 염의 제조방법 | |
US4428806A (en) | Process for producing brominated 1,3-dioxolen-2-ones | |
CN106243079B (zh) | 双环醇的制备方法及其中间体化合物 | |
US10144692B2 (en) | Method of making vitamin K1 | |
JP3338101B2 (ja) | アリールアクリル酸類及びそれらのエステル類の製造方法 | |
KR20030005394A (ko) | 트리플루오로에톡시-치환된 벤조산의 제조 방법 | |
CN108727187A (zh) | 一种(r)-(+)-2-对羟基苯氧基丙酸的制备方法 | |
JPH03279348A (ja) | 2,4,5―トリフルオロ―3―アルコキシ安息香酸の製造方法 | |
KR102333606B1 (ko) | 1-팔미토일-2-리놀레오일-3-아세틸 글리세롤의 제조 방법 | |
US4730077A (en) | Method of preparing α-arylalkanoic esters | |
CA2348412C (en) | A process for the preparation of alpha-arylalkanoic acids | |
JP2599958B2 (ja) | 含フッ素イソフタル酸ジエステル | |
JP3254746B2 (ja) | 末端アセチレン化合物およびその製造法 | |
ITMI992534A1 (it) | Procedimento per la preparazione di eteri derivati da acidididrossibenzoici | |
JP2001011015A (ja) | 酒石酸低級アルキルジエステルの製造法 | |
JP2762643B2 (ja) | 4―ヒドロキシシクロペンテノン誘導体の製造方法 | |
JP2581186B2 (ja) | 4−置換−2−シクロペンテノンエステル誘導体の製造法 | |
US3646104A (en) | Method for the ring cleavage of 2 6-dioximinocyclohexanone | |
CN116120238A (zh) | 一种咪唑衍生物的制备方法 | |
JPH0372054B2 (ko) | ||
JPH1171325A (ja) | 4−アリールブタン酸アルキルエステル類の製造方法 | |
JPS63190855A (ja) | メタクリル酸エステルの製造方法 | |
EP3409657A1 (en) | Method for producing acid halide solution and method for producing monoester compound |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A201 | Request for examination | ||
E902 | Notification of reason for refusal | ||
E902 | Notification of reason for refusal | ||
E701 | Decision to grant or registration of patent right | ||
GRNT | Written decision to grant | ||
FPAY | Annual fee payment |
Payment date: 20120927 Year of fee payment: 11 |
|
FPAY | Annual fee payment |
Payment date: 20130927 Year of fee payment: 12 |
|
FPAY | Annual fee payment |
Payment date: 20140929 Year of fee payment: 13 |
|
FPAY | Annual fee payment |
Payment date: 20150930 Year of fee payment: 14 |
|
FPAY | Annual fee payment |
Payment date: 20160929 Year of fee payment: 15 |
|
FPAY | Annual fee payment |
Payment date: 20180928 Year of fee payment: 17 |
|
EXPY | Expiration of term |