SU617005A3 - Method of obtaining 2-(6-carbomethoxyhexyl)-4-(r)-oxycyclopentenone-2 - Google Patents
Method of obtaining 2-(6-carbomethoxyhexyl)-4-(r)-oxycyclopentenone-2Info
- Publication number
- SU617005A3 SU617005A3 SU731975423A SU1975423A SU617005A3 SU 617005 A3 SU617005 A3 SU 617005A3 SU 731975423 A SU731975423 A SU 731975423A SU 1975423 A SU1975423 A SU 1975423A SU 617005 A3 SU617005 A3 SU 617005A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- carbomethoxyhexyl
- oxycyclopentenone
- obtaining
- acetic acid
- reaction mixture
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- -1 6-carbomethoxyhexyl Chemical group 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PIBGGWWVVJELOD-UHFFFAOYSA-N 2-hex-5-enoxyacetic acid Chemical compound OC(=O)COCCCCC=C PIBGGWWVVJELOD-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229940125585 NDV-HXP-S Drugs 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
25 мл cyxoio ацетона. Смесь наг()евают в атмосфере азота 24 часа. После охлаждени реакционную смесь разбав.г ют эти.ювым эф ром и :|фнрн1)1Й слой промывают последовательно водой, содой, водой и насыщенным раствором хлористого натри . Слой растворител сушат над безводны.м с.ульфатом иатри и вынаривают досуха, получают 560 мг масл нистого остатка. Остаток перекрнсталлизов| 1ваюг из изопропилового эфира и получают 316 мг (53%) 1-изопроиокси-2-(6-карбометоксигексил, -4-(R)-цпклопентеи-3-она, т.пл. 60-62°С, 259 нм ( 20,600). К i23 .virO,412 (ммол ) 1-изопропокси-2-(6-карбометоксигексил ) -4- (R) -оксициклопентен-3 -она в 10 мл тетрагидрофурана, в атмосфере азрта ири температуре -7НС. добавл ют четыре раза по 1,1 мл (1,5 мм().1 ) бензо.чьно о раствора патрий дигидро бнс-(метокс1Г51ТОКС111 -алюмината по капл м в течение 7 мин. Реакционную с.месь пере.мешивают при -7ЬС 45 мин, а затем добавл ют 2 .мл уксуспой кис-, лоты. Реакционна с.месь нагреваете до комнатной температуры и ее выпаривают досуха. Зате.м добав.ч ют 10 мл 75 Vo-иoгo раствора уксусной кислоты, перемешивают 24 час. Уксусную кислоту и ВОД)- выпаривают под давление .м. Полученное .маслообразное вещество |)асгвор ют в 25 .мл этн,1ацетата, промывают насьицеппыми растворо.м хлористого натри , а затем высушивают над сульфатом магни . Кристаллизацией остатка из эти.1аиетата получают 60 мг 2-(6-карбометокснгекси.,ч)-4-(R)-цикл ()нентен-2-она, выход 49.Vi. |.нл. 60- fil4/ faJH, + 17,82 (С. 0,49 (); УФХ, 222 н.м ( 8.400); циркул рному днхроизму 231 нм н -9,9 X И)-- (.VleOMi. Проведение 0-алкилировани 2-(6-карб)метоксигексил ) -4- (R) -оксициклопентанлиона-1,3 с последующим восстановлением продукта O-a.iкилиронани позвол ет увеличить вьгход целевого продукта до 49%. Формула ii.KJopeTeHiifi Способ полученп 2-(()-карбо.метоксигексил ) -4; ( R) -оксициклопентеиона-2 на осио1н 2- (6-карбомстокс1 гексил) -4- (R) -оке и ци клонентаидиопа-1 ,3 с нри.менением восстановлени производных ено. ()1ормы 2-(6-карбо.метокснгекси ,) -4- (R) -окснцик.юпептандиона-1,3, отличающийс те.м, что. с целью уве.шчепн выхода целевого нродукта, 2-(6-карбометоксигексил ) -4- ( R) -окс11Циклопе1ггапди(Л1-1,3 подвергают О-алки.1ированию изопр()пи,1йод||дом при рН от 7.5 до 10 II подвергают восгтановленню полученный прп это.м l-n:ionponoKcn-2-()о .метоксигексп.) -4- ( R) -oKcii-2--nnK.i()neineii-.. Иеточники информации, прин тые во вии.маиие при экспертизе: 1. Патент США JVo 377:5622. K.I. i9.i;51P: 1973.25 ml of cyxoio acetone. A mixture of nag () is eaten under nitrogen for 24 hours. After cooling, the reaction mixture is diluted with this syrup and: Phn1) The 1 st layer is washed successively with water, soda, water, and saturated sodium chloride solution. The solvent layer is dried over anhydrous s. Sulphate and sodium and taken to dryness to obtain 560 mg of an oily residue. Remaining cross-install | 1vayug from isopropyl ether and get 316 mg (53%) of 1-isopiroxy-2- (6-carbomethoxyhexyl, -4- (R) -cpklopentei-3-it, so pl. 60-62 ° C, 259 nm (20,600 ) To i23 .virO, 412 (mmol) 1-isopropoxy-2- (6-carbomethoxyhexyl) -4- (R) -oxycyclopentene-3-one in 10 ml of tetrahydrofuran, in an atmosphere of azrat, and -7H temperature. 1.1 ml times (1.5 mm (). 1) benzo.chno about a solution of patria dihydro bns- (methoxyG51TOX111-aluminate dropwise within 7 minutes. The reaction mixture is stirred at -7 ° C for 45 minutes, and then add 2 ml. of acetic acid, lots. The reaction mixture is heated to room temperature. the temperature and evaporate it to dryness. Then add 10 ml of 75 Vo-acetic acid solution, mix for 24 hours. Acetic acid and BOD) are evaporated under pressure. The resulting oil is obtained in 25. ml of ethn, 1 acetate, washed with sodium chloride m-sodium chloride, and then dried over magnesium sulfate. By crystallization of the residue from these. 1 aietate, 60 mg of 2- (6-carbomethoxane hexxy., H) -4- (R) -cycle () nenthen-2-one is obtained, yield 49. Vi. | .nl. 60- fil4 / faJH, + 17.82 (p. 0.49 (); UFH, 222 Nm (8.400); to a circular dhronism of 231 nm n -9.9 X I) - (.VleOMi. Conduction 0 -alkylation of 2- (6-carb) methoxyhexyl) -4- (R) -oxycyclopentanlion-1,3, followed by reduction of the product Oa.iquilirovania allows increasing the consumption of the desired product to 49%. Formula ii.KJopeTeHiifi Method received 2 - (() - carbo.methoxyhexyl) -4; (R) -oxycyclopenteion-2 on osio1n 2- (6-carbomsox-1 hexyl) -4- (R) -oke and cyclonentadiopa-1, 3 with a change in the reduction of the derivatives eno. () The norms of 2- (6-carboxymethoxyhexene,) -4- (R) -oxncyc.yuptanedione-1,3, differing in that.m. in order to increase the yield of the target product, 2- (6-carbomethoxyhexyl) -4- (R) -ox11 Cyclopellgapdi (L1-1.3 is subjected to O-alkyrization with isopr () pi, 1y || 10 II subject the received ppp it. M ln: ionponoKcn-2 - () o. Methoxyhexp.) -4- (R) -oKcii-2 - nnK.i () neineii- .. Integrals of information received Weigh in examination: 1. US Patent JVo 377: 5622. K.I. i9.i; 51P: 1973.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30976672A | 1972-11-27 | 1972-11-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU617005A3 true SU617005A3 (en) | 1978-07-25 |
Family
ID=23199601
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU731975423A SU617005A3 (en) | 1972-11-27 | 1973-11-26 | Method of obtaining 2-(6-carbomethoxyhexyl)-4-(r)-oxycyclopentenone-2 |
Country Status (25)
| Country | Link |
|---|---|
| JP (1) | JPS5328908B2 (en) |
| AR (1) | AR198543A1 (en) |
| AT (1) | AT330143B (en) |
| AU (1) | AU459800B2 (en) |
| BE (1) | BE807825A (en) |
| BG (1) | BG21204A3 (en) |
| CA (1) | CA1034139A (en) |
| CH (1) | CH599098A5 (en) |
| CS (1) | CS170480B2 (en) |
| DD (1) | DD108516A5 (en) |
| DE (1) | DE2358781C3 (en) |
| ES (1) | ES420855A1 (en) |
| FR (1) | FR2207905B1 (en) |
| GB (1) | GB1440108A (en) |
| HU (1) | HU169638B (en) |
| IE (1) | IE38497B1 (en) |
| IL (1) | IL43597A (en) |
| NL (1) | NL7316147A (en) |
| NO (1) | NO138905C (en) |
| PH (1) | PH10276A (en) |
| PL (1) | PL91162B1 (en) |
| RO (1) | RO63011A (en) |
| SE (1) | SE406462B (en) |
| SU (1) | SU617005A3 (en) |
| ZA (1) | ZA738581B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU529883B2 (en) * | 1978-09-04 | 1983-06-23 | Australian National University, The | Substituted cyclopentenones |
| JPS56159683U (en) * | 1980-04-28 | 1981-11-28 | ||
| US5227505A (en) * | 1987-06-16 | 1993-07-13 | Nissan Chemical Industries, Ltd. | Substituted cyclic ketones, substituted cyclic enones, and process for producing the same |
| JP2696933B2 (en) * | 1987-06-16 | 1998-01-14 | 日産化学工業株式会社 | Substituted cyclic ketones and substituted cyclic enones and methods for their preparation |
| US5254708A (en) * | 1987-06-16 | 1993-10-19 | Nissan Chemical Industries, Ltd. | Substituted cyclic ketones, substituted cyclic enones, and process for producing the same |
| US5231208A (en) * | 1987-06-16 | 1993-07-27 | Nissan Chemical Industries, Ltd. | Substituted cyclic ketones, substituted cyclic enones, and process for producing the same |
-
1973
- 1973-11-07 CA CA185,210A patent/CA1034139A/en not_active Expired
- 1973-11-07 IE IE2003/73A patent/IE38497B1/en unknown
- 1973-11-08 AU AU62283/73A patent/AU459800B2/en not_active Expired
- 1973-11-08 IL IL43597A patent/IL43597A/en unknown
- 1973-11-08 ZA ZA738581A patent/ZA738581B/en unknown
- 1973-11-09 GB GB5222073A patent/GB1440108A/en not_active Expired
- 1973-11-15 PH PH15227A patent/PH10276A/en unknown
- 1973-11-16 AR AR251028A patent/AR198543A1/en active
- 1973-11-20 CH CH1628373A patent/CH599098A5/xx not_active IP Right Cessation
- 1973-11-22 AT AT980073A patent/AT330143B/en not_active IP Right Cessation
- 1973-11-22 JP JP13086973A patent/JPS5328908B2/ja not_active Expired
- 1973-11-26 DE DE2358781A patent/DE2358781C3/en not_active Expired
- 1973-11-26 DD DD174893A patent/DD108516A5/en unknown
- 1973-11-26 BG BG025076A patent/BG21204A3/en unknown
- 1973-11-26 ES ES420855A patent/ES420855A1/en not_active Expired
- 1973-11-26 SU SU731975423A patent/SU617005A3/en active
- 1973-11-26 NL NL7316147A patent/NL7316147A/xx unknown
- 1973-11-26 HU HUWI246A patent/HU169638B/hu unknown
- 1973-11-26 BE BE138190A patent/BE807825A/en not_active IP Right Cessation
- 1973-11-26 FR FR7341997A patent/FR2207905B1/fr not_active Expired
- 1973-11-26 NO NO734495A patent/NO138905C/en unknown
- 1973-11-26 SE SE737315982A patent/SE406462B/en unknown
- 1973-11-26 RO RO7300076778A patent/RO63011A/en unknown
- 1973-11-26 PL PL1973166812A patent/PL91162B1/en unknown
- 1973-11-26 CS CS8114A patent/CS170480B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE406462B (en) | 1979-02-12 |
| JPS5328908B2 (en) | 1978-08-17 |
| JPS4982649A (en) | 1974-08-08 |
| AT330143B (en) | 1976-06-10 |
| NO138905B (en) | 1978-08-28 |
| NO138905C (en) | 1978-12-06 |
| AU459800B2 (en) | 1975-04-10 |
| AU6228373A (en) | 1975-04-10 |
| IL43597A0 (en) | 1974-03-14 |
| GB1440108A (en) | 1976-06-23 |
| HU169638B (en) | 1976-12-28 |
| IE38497L (en) | 1974-05-27 |
| PH10276A (en) | 1976-11-03 |
| ATA980073A (en) | 1975-09-15 |
| CH599098A5 (en) | 1978-05-12 |
| DD108516A5 (en) | 1974-09-20 |
| DE2358781C3 (en) | 1979-11-08 |
| FR2207905A1 (en) | 1974-06-21 |
| IE38497B1 (en) | 1978-03-29 |
| IL43597A (en) | 1976-09-30 |
| RO63011A (en) | 1978-05-15 |
| DE2358781A1 (en) | 1974-06-12 |
| ES420855A1 (en) | 1976-04-01 |
| DE2358781B2 (en) | 1979-01-25 |
| NL7316147A (en) | 1974-05-29 |
| BG21204A3 (en) | 1976-03-20 |
| ZA738581B (en) | 1974-09-25 |
| AR198543A1 (en) | 1974-06-28 |
| FR2207905B1 (en) | 1978-02-24 |
| BE807825A (en) | 1974-03-15 |
| CS170480B2 (en) | 1976-08-27 |
| CA1034139A (en) | 1978-07-04 |
| PL91162B1 (en) | 1977-02-28 |
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