CN105906486B - 沙格雷酯中间体2‑[2‑(3‑甲氧基苯基)乙基]苯酚的合成方法 - Google Patents
沙格雷酯中间体2‑[2‑(3‑甲氧基苯基)乙基]苯酚的合成方法 Download PDFInfo
- Publication number
- CN105906486B CN105906486B CN201610251703.0A CN201610251703A CN105906486B CN 105906486 B CN105906486 B CN 105906486B CN 201610251703 A CN201610251703 A CN 201610251703A CN 105906486 B CN105906486 B CN 105906486B
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- CN
- China
- Prior art keywords
- ethyl
- phenol
- methoxyphenyls
- product
- sarpogrelate
- 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.)
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- FFYNAVGJSYHHFO-UHFFFAOYSA-N sarpogrelate Chemical compound COC1=CC=CC(CCC=2C(=CC=CC=2)OCC(CN(C)C)OC(=O)CCC(O)=O)=C1 FFYNAVGJSYHHFO-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 229950005789 sarpogrelate Drugs 0.000 title claims abstract description 11
- 238000010189 synthetic method Methods 0.000 title claims abstract description 7
- HGQQRAXOBYWKDV-UHFFFAOYSA-N 2-[2-(3-methoxyphenyl)ethyl]phenol Chemical compound COC1=CC=CC(CCC=2C(=CC=CC=2)O)=C1 HGQQRAXOBYWKDV-UHFFFAOYSA-N 0.000 title abstract 3
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 9
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 claims abstract description 7
- PBEJTRAJWCNHRS-UHFFFAOYSA-N 2-phenylmethoxybenzaldehyde Chemical group O=CC1=CC=CC=C1OCC1=CC=CC=C1 PBEJTRAJWCNHRS-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000003208 petroleum Substances 0.000 claims abstract description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 15
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 238000001914 filtration Methods 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 5
- 239000004519 grease Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 238000001514 detection method Methods 0.000 claims description 3
- 235000019441 ethanol Nutrition 0.000 claims description 3
- 125000005909 ethyl alcohol group Chemical group 0.000 claims description 3
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 238000001291 vacuum drying Methods 0.000 claims description 3
- 238000010792 warming Methods 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract description 6
- 239000012535 impurity Substances 0.000 abstract description 3
- 240000000203 Salix gracilistyla Species 0.000 abstract description 2
- 238000009833 condensation Methods 0.000 abstract description 2
- 230000005494 condensation Effects 0.000 abstract description 2
- 238000005984 hydrogenation reaction Methods 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 235000021419 vinegar Nutrition 0.000 abstract description 2
- 239000000052 vinegar Substances 0.000 abstract description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical class COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
- 230000002785 anti-thrombosis Effects 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 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 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/141—Esters of phosphorous acids
- C07F9/1414—Esters of phosphorous acids with arylalkanols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/20—Preparation of ethers by reactions not forming ether-oxygen bonds by hydrogenation of carbon-to-carbon double or triple bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (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)
Abstract
Description
Claims (1)
Priority Applications (1)
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CN201610251703.0A CN105906486B (zh) | 2016-04-20 | 2016-04-20 | 沙格雷酯中间体2‑[2‑(3‑甲氧基苯基)乙基]苯酚的合成方法 |
Applications Claiming Priority (1)
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CN201610251703.0A CN105906486B (zh) | 2016-04-20 | 2016-04-20 | 沙格雷酯中间体2‑[2‑(3‑甲氧基苯基)乙基]苯酚的合成方法 |
Publications (2)
Publication Number | Publication Date |
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CN105906486A CN105906486A (zh) | 2016-08-31 |
CN105906486B true CN105906486B (zh) | 2018-04-20 |
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CN201610251703.0A Active CN105906486B (zh) | 2016-04-20 | 2016-04-20 | 沙格雷酯中间体2‑[2‑(3‑甲氧基苯基)乙基]苯酚的合成方法 |
Country Status (1)
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CN (1) | CN105906486B (zh) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
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CN107324979A (zh) * | 2017-08-16 | 2017-11-07 | 北京奥得赛化学股份有限公司 | 一种盐酸沙格雷酯中间体的制备方法 |
CN114394905A (zh) * | 2019-03-18 | 2022-04-26 | 安徽峆一药业股份有限公司 | 盐酸沙格雷酯中间体2-(3-二甲氨基-2-羟基)丙氧基苯甲醛的合成方法 |
CN109824527A (zh) * | 2019-03-18 | 2019-05-31 | 安徽峆一药业股份有限公司 | 一种盐酸沙格雷酯的合成方法 |
Family Cites Families (1)
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CN105439828B (zh) * | 2015-12-30 | 2018-10-23 | 苏州诚和医药化学有限公司 | 合成1-苄氧基-2-[2-(3-甲氧基苯基)乙烯基]苯的方法 |
-
2016
- 2016-04-20 CN CN201610251703.0A patent/CN105906486B/zh active Active
Non-Patent Citations (2)
Title |
---|
A practical synthesis of sarpogrelate hydrochloride and in vitro platelet aggregation inhibitory activities of its analogues;Guo Hua Chen等;《Chinese Chemical Letters》;20100106;第21卷(第3期);第288页Scheme 1 * |
白藜芦醇的化学合成研究;王世盛等;《中国药物化学杂质》;20040430;第14卷(第2期);第91页右栏,Fig 1;第92页右栏1.4-1.5部分 * |
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CB02 | Change of applicant information |
Address after: 239300 Yang Cun Industrial Zone, Chuzhou, Anhui, Tianchang Applicant after: Anhui He pharmaceutical Limited by Share Ltd Address before: 239300 Yang Cun Industrial Zone, Chuzhou, Anhui, Tianchang Applicant before: Anhui Heryi Chemicals Co., Ltd. |
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CB02 | Change of applicant information | ||
TA01 | Transfer of patent application right |
Effective date of registration: 20180319 Address after: 239311 fine chemical concentrated area of Tianchang copper town in Chuzhou, Anhui Applicant after: Anhui Xiu Yi Pharmaceutical Co., Ltd. Address before: 239300 Yang Cun Industrial Zone, Chuzhou, Anhui, Tianchang Applicant before: Anhui He pharmaceutical Limited by Share Ltd |
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