CN103012386A - 一种五元环状硫酸酯的制备方法 - Google Patents
一种五元环状硫酸酯的制备方法 Download PDFInfo
- Publication number
- CN103012386A CN103012386A CN2012105766198A CN201210576619A CN103012386A CN 103012386 A CN103012386 A CN 103012386A CN 2012105766198 A CN2012105766198 A CN 2012105766198A CN 201210576619 A CN201210576619 A CN 201210576619A CN 103012386 A CN103012386 A CN 103012386A
- Authority
- CN
- China
- Prior art keywords
- membered cyclic
- preparation
- sulfuric ester
- oxone
- reaction
- 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
- 125000004122 cyclic group Chemical group 0.000 title claims abstract description 39
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 title abstract 5
- 229910021653 sulphate ion Inorganic materials 0.000 title abstract 5
- 239000003960 organic solvent Substances 0.000 claims abstract description 11
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims abstract description 9
- 230000001590 oxidative effect Effects 0.000 claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims description 43
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 30
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 24
- 150000002148 esters Chemical class 0.000 claims description 24
- 239000007864 aqueous solution Substances 0.000 claims description 19
- 239000002994 raw material Substances 0.000 claims description 14
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 12
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 15
- 238000007254 oxidation reaction Methods 0.000 abstract description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 5
- 239000000460 chlorine Substances 0.000 abstract description 5
- 229910052801 chlorine Inorganic materials 0.000 abstract description 5
- 229910052751 metal Inorganic materials 0.000 abstract description 5
- 239000002184 metal Substances 0.000 abstract description 5
- 239000007800 oxidant agent Substances 0.000 abstract description 4
- 239000003814 drug Substances 0.000 abstract description 3
- 230000002194 synthesizing effect Effects 0.000 abstract description 2
- 229940079593 drug Drugs 0.000 abstract 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 abstract 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000001514 detection method Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 238000007086 side reaction Methods 0.000 description 5
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 4
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 4
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 4
- NYPIRLYMDJMKGW-VPCXQMTMSA-N 4-amino-1-[(2r,3r,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyloxolan-2-yl]pyrimidin-2-one Chemical compound C[C@@]1(F)[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)N=C(N)C=C1 NYPIRLYMDJMKGW-VPCXQMTMSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000012467 final product Substances 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- -1 tetramethyl piperidine oxide compound Chemical class 0.000 description 2
- QBCFVMMTZAQUDY-UHFFFAOYSA-N CCOC(C(C)(C(C(C(O)=S=O)O)O)O)=O Chemical compound CCOC(C(C)(C(C(C(O)=S=O)O)O)O)=O QBCFVMMTZAQUDY-UHFFFAOYSA-N 0.000 description 1
- 0 CCO[S@](OC(*)[C@@]1OC(C)(*)OC1)=CC Chemical compound CCO[S@](OC(*)[C@@]1OC(C)(*)OC1)=CC 0.000 description 1
- 208000005176 Hepatitis C Diseases 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000003827 glycol group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000007344 nucleophilic reaction Methods 0.000 description 1
- 239000012434 nucleophilic reagent Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 150000003410 sphingosines Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Description
Claims (9)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201210576619.8A CN103012386B (zh) | 2012-12-26 | 2012-12-26 | 一种五元环状硫酸酯的制备方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201210576619.8A CN103012386B (zh) | 2012-12-26 | 2012-12-26 | 一种五元环状硫酸酯的制备方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN103012386A true CN103012386A (zh) | 2013-04-03 |
CN103012386B CN103012386B (zh) | 2015-04-01 |
Family
ID=47961540
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201210576619.8A Active CN103012386B (zh) | 2012-12-26 | 2012-12-26 | 一种五元环状硫酸酯的制备方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN103012386B (zh) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104945286A (zh) * | 2015-06-25 | 2015-09-30 | 成都百事兴科技实业有限公司 | 一种高纯度硫酸二酯的合成方法 |
CN105175391A (zh) * | 2015-10-19 | 2015-12-23 | 安徽金太阳生化药业有限公司 | 一种以金纳米粒子催化氧化制备环硫酸酯的方法 |
CN109422719A (zh) * | 2017-08-30 | 2019-03-05 | 张家港市国泰华荣化工新材料有限公司 | 环状硫酸酯的制备方法 |
CN110386916A (zh) * | 2019-07-23 | 2019-10-29 | 常熟市常吉化工有限公司 | 一种环状硫酸酯的合成方法 |
CN111763200A (zh) * | 2020-07-13 | 2020-10-13 | 香河昆仑化学制品有限公司 | 一种锂离子电池电解液添加剂环碳酸硫酸乙烯酯及其制备方法 |
CN112159388A (zh) * | 2020-09-30 | 2021-01-01 | 湖南阿斯达新材料有限公司 | 一种硫酸乙烯酯衍生物的制备方法 |
CN115322170A (zh) * | 2022-08-29 | 2022-11-11 | 苏州华一新能源科技股份有限公司 | 一种硫酸乙烯酯的制备方法 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4820848A (en) * | 1984-12-12 | 1989-04-11 | Merck & Co., Inc. | Substituted aromatic sulfonamides as antiglaucoma agents |
US6172057B1 (en) * | 1997-02-27 | 2001-01-09 | American Cyanamid Company | N-Hydroxy-2-(alkyl, aryl, or heteroaryl sulfanyl, sulfinyl or sulfonyl)-3-substituted alkyl, aryl or heteroarylamides as matrix metalloproteinase inhibitors |
CN1665795A (zh) * | 2002-07-03 | 2005-09-07 | 拜尔农作物科学股份公司 | 杂环氟代链烯基砜的制备方法 |
EP1918293A1 (en) * | 2006-10-02 | 2008-05-07 | Sandoz AG | Process for the preparation of 6-substituted-4-oxo-thieno [2,3b]thiopyran-2-sulfonic acid |
CN101600725A (zh) * | 2006-10-10 | 2009-12-09 | 法莫赛特股份有限公司 | 制备呋喃核糖基嘧啶核苷 |
CN102656154A (zh) * | 2009-12-18 | 2012-09-05 | 天秤医药股份有限公司 | 用于制备取代的1-O-酰基-2-脱氧-2-氟-4-硫代-β-D-***呋喃糖的方法 |
-
2012
- 2012-12-26 CN CN201210576619.8A patent/CN103012386B/zh active Active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4820848A (en) * | 1984-12-12 | 1989-04-11 | Merck & Co., Inc. | Substituted aromatic sulfonamides as antiglaucoma agents |
US6172057B1 (en) * | 1997-02-27 | 2001-01-09 | American Cyanamid Company | N-Hydroxy-2-(alkyl, aryl, or heteroaryl sulfanyl, sulfinyl or sulfonyl)-3-substituted alkyl, aryl or heteroarylamides as matrix metalloproteinase inhibitors |
CN1665795A (zh) * | 2002-07-03 | 2005-09-07 | 拜尔农作物科学股份公司 | 杂环氟代链烯基砜的制备方法 |
EP1918293A1 (en) * | 2006-10-02 | 2008-05-07 | Sandoz AG | Process for the preparation of 6-substituted-4-oxo-thieno [2,3b]thiopyran-2-sulfonic acid |
CN101600725A (zh) * | 2006-10-10 | 2009-12-09 | 法莫赛特股份有限公司 | 制备呋喃核糖基嘧啶核苷 |
CN102656154A (zh) * | 2009-12-18 | 2012-09-05 | 天秤医药股份有限公司 | 用于制备取代的1-O-酰基-2-脱氧-2-氟-4-硫代-β-D-***呋喃糖的方法 |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104945286A (zh) * | 2015-06-25 | 2015-09-30 | 成都百事兴科技实业有限公司 | 一种高纯度硫酸二酯的合成方法 |
CN105175391A (zh) * | 2015-10-19 | 2015-12-23 | 安徽金太阳生化药业有限公司 | 一种以金纳米粒子催化氧化制备环硫酸酯的方法 |
CN105175391B (zh) * | 2015-10-19 | 2018-04-20 | 安徽金太阳生化药业有限公司 | 一种以金纳米粒子催化氧化制备环硫酸酯的方法 |
CN109422719A (zh) * | 2017-08-30 | 2019-03-05 | 张家港市国泰华荣化工新材料有限公司 | 环状硫酸酯的制备方法 |
CN110386916A (zh) * | 2019-07-23 | 2019-10-29 | 常熟市常吉化工有限公司 | 一种环状硫酸酯的合成方法 |
CN111763200A (zh) * | 2020-07-13 | 2020-10-13 | 香河昆仑化学制品有限公司 | 一种锂离子电池电解液添加剂环碳酸硫酸乙烯酯及其制备方法 |
CN112159388A (zh) * | 2020-09-30 | 2021-01-01 | 湖南阿斯达新材料有限公司 | 一种硫酸乙烯酯衍生物的制备方法 |
CN112159388B (zh) * | 2020-09-30 | 2022-10-11 | 湖南阿斯达新材料有限公司 | 一种硫酸乙烯酯衍生物的制备方法 |
CN115322170A (zh) * | 2022-08-29 | 2022-11-11 | 苏州华一新能源科技股份有限公司 | 一种硫酸乙烯酯的制备方法 |
Also Published As
Publication number | Publication date |
---|---|
CN103012386B (zh) | 2015-04-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN103012386B (zh) | 一种五元环状硫酸酯的制备方法 | |
CN103880596B (zh) | 一种适合工业化生产的硝酸布康唑中间体的制备方法 | |
CN103073536B (zh) | 一种艾普拉唑的制备方法 | |
CN101786948A (zh) | 1-(4-氯苯基)-2-环丙基-1-丙酮的制备方法 | |
CN105085544A (zh) | 一种他唑巴坦二苯甲酯的合成方法 | |
CN103360316A (zh) | 一种氟虫腈的制备方法 | |
CN109942539A (zh) | 一种2-氟-1,3-丙磺酸内酯的制备方法 | |
KR101705210B1 (ko) | 클로로히드린류 조성물의 제조방법 및 그 방법에 의해 제조된 클로로히드린류 조성물을 사용하는 에피클로로히드린의 제조방법 | |
CN109369487B (zh) | 一种高纯度斑蝥黄制备方法 | |
CN106749335B (zh) | 一种卤代氧头孢类中间体的制备方法和应用 | |
CN103172479B (zh) | 一种钯催化的联芳烃制备方法 | |
CN100503588C (zh) | 一种从轻质油中回收环氧环己烷工艺的开环反应方法 | |
CN101891693B (zh) | 一种氟康唑的制备方法 | |
CN103664739B (zh) | 一种特拉匹韦中间体的制备方法 | |
CN107540531A (zh) | 一种利用环己酮副产轻质油制备邻氯环己酮的方法 | |
CN104736517A (zh) | 制备烷氧羰基异硫氰酸酯的方法 | |
CN109678770B (zh) | 一种β-胡萝卜素氧化制备斑蝥黄的方法 | |
CN106749098A (zh) | 一种以氧气为氧化剂制备盐酸二氧丙嗪的绿色工艺 | |
CN101475541B (zh) | 4-甲基噻唑-5-羧酸的一种制备方法 | |
CN102344419A (zh) | 广谱抗真菌药氟康唑的制备方法 | |
CN102329235B (zh) | 一种对硝基苯甲醛的生产工艺 | |
CN103408438A (zh) | 2-羟基-3-丁烯-1-胺的分离纯化方法 | |
CN103183592A (zh) | 2-氯-1,1,1-三烷氧基乙烷的制备方法 | |
CN104876872B (zh) | 一种制备1‑叔丁氧基羰基‑3‑羟甲基吲唑的方法及应用 | |
CN103012170A (zh) | 一种4-甲氧基苯乙胺的制备方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
ASS | Succession or assignment of patent right |
Owner name: ZHEJIANG PULUO DEBANG PHARMACEUTICAL CO., LTD. Free format text: FORMER OWNER: ZHEJIANG APELOA CHEMICAL CO., LTD. Effective date: 20150206 |
|
C41 | Transfer of patent application or patent right or utility model | ||
TA01 | Transfer of patent application right |
Effective date of registration: 20150206 Address after: 322118 Dongyang Jiangnan Road, Hengdian Industrial Zone, Zhejiang, China, No. 519, No. Applicant after: Zhejiang Puluo Debang Pharmaceutical Co., Ltd. Address before: 322118 Dongyang Jiangnan Road, Hengdian Industrial Zone, Zhejiang, China, No. 519, No. Applicant before: Zhejiang Apeloa Chemical Co., Ltd. |
|
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
TR01 | Transfer of patent right |
Effective date of registration: 20200629 Address after: 322118, 519, Zhenjiang South Road, Dongyang, Zhejiang, Jinhua, Hengdian Co-patentee after: APELOA PHARMACEUTICAL Co.,Ltd. Patentee after: ZHEJIANG APELOA TOSPO PHARMACEUTICAL Co.,Ltd. Address before: 322118, Jiangnan Road 519, Hengdian Industrial Zone, Jinhua, Zhejiang, Dongyang Patentee before: ZHEJIANG APELOA TOSPO PHARMACEUTICAL Co.,Ltd. |
|
TR01 | Transfer of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: A preparation method of five membered cyclic sulfate Effective date of registration: 20210922 Granted publication date: 20150401 Pledgee: Dongyang sub branch of Bank of China Ltd. Pledgor: ZHEJIANG APELOA TOSPO PHARMACEUTICAL Co.,Ltd. Registration number: Y2021330001744 |