CS195615B1 - Method of producing derivatives of 3-hydroxy-2-phenylpropionic acid - Google Patents
Method of producing derivatives of 3-hydroxy-2-phenylpropionic acid Download PDFInfo
- Publication number
- CS195615B1 CS195615B1 CS238578A CS238578A CS195615B1 CS 195615 B1 CS195615 B1 CS 195615B1 CS 238578 A CS238578 A CS 238578A CS 238578 A CS238578 A CS 238578A CS 195615 B1 CS195615 B1 CS 195615B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- acid
- formula
- hydroxy
- ethyl ester
- ester
- Prior art date
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- JACRWUWPXAESPB-UHFFFAOYSA-N tropic acid Chemical class OCC(C(O)=O)C1=CC=CC=C1 JACRWUWPXAESPB-UHFFFAOYSA-N 0.000 title claims description 4
- 238000000034 method Methods 0.000 title description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000004494 ethyl ester group Chemical group 0.000 claims description 5
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- 229920002866 paraformaldehyde Polymers 0.000 claims description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 4
- -1 3-hydroxy-2-isopropylpentylphenylpropionic acid Chemical compound 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 2
- 239000007864 aqueous solution Substances 0.000 claims 2
- 230000020477 pH reduction Effects 0.000 claims 2
- CKIPXLZSJUHFDD-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-hydroxypropanoic acid Chemical compound OCC(C(O)=O)C1=CC=C(Cl)C=C1 CKIPXLZSJUHFDD-UHFFFAOYSA-N 0.000 claims 1
- GSVPDLNMVPXACN-UHFFFAOYSA-N 3-hydroxy-2-[4-(2-methylpropyl)phenyl]propanoic acid Chemical compound CC(C)CC1=CC=C(C(CO)C(O)=O)C=C1 GSVPDLNMVPXACN-UHFFFAOYSA-N 0.000 claims 1
- DULCUDSUACXJJC-UHFFFAOYSA-N Ethyl phenylacetate Chemical compound CCOC(=O)CC1=CC=CC=C1 DULCUDSUACXJJC-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- LFMYKNVKLMQSJV-UHFFFAOYSA-N ethyl 2-(4-propan-2-ylphenyl)acetate Chemical compound CCOC(=O)CC1=CC=C(C(C)C)C=C1 LFMYKNVKLMQSJV-UHFFFAOYSA-N 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229960003424 phenylacetic acid Drugs 0.000 description 2
- 239000003279 phenylacetic acid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- CVZHTBMFVPENFE-UHFFFAOYSA-N 2-(4-chlorophenyl)butanoic acid Chemical compound CCC(C(O)=O)C1=CC=C(Cl)C=C1 CVZHTBMFVPENFE-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-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
- 239000003513 alkali Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical class CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
POPIS VYNALEZU K AUTORSKÉMU OSVĚDČENÍDESCRIPTION COMPLETED WITH COPYRIGHT CERTIFICATE
ČESKOSLOVENSKASOCIALISTICKÁREPUBLIKA( 1» ) 195615 (11) (Bl)CZECHOSLOVAKCASOCIALISTREPUBLIC (1 ») 195615 (11) (Bl)
/22/ Přihlášeno 12 04 78/21/ /PV 2385-78/ (,|HI Zveřejněno 31 05 79/ 22 / Registered 12 04 78/21 / / PV 2385-78 / (, | HI Published 31 05 79
ÚŘAD PRO VYNÁLEZY (45) Vydáno 1 5 04 8 2OFFICE OFFICE (45) Issued 1 5 04 8 2
A OBJEVY (75) -AND DISCOVERY (75) -
Autor vynálezu FIŠNEROVÁ LUDMILA ing. CSc. a NĚMEČEK OLDŘICH dr. ing. DrSc., PVAHA (54) Způsob výroby derivátů kyseliny 3-hydroxy-2-fenylpropionovóAuthor of the Invention FIŠNEROVÁ LUDMILA ing. CSc. and NĚMEČEK OLDŘICH dr. DrSc., PVAHA (54) Method of production of 3-hydroxy-2-phenylpropionic acid derivatives
Vynález se týká způsobu výroby nových de-rivátů kyseliny 3-hydroxy-2-fenylpropi.onovéobecného vzorce I ,-A-c R_^J^_CHCOOCaH5 /111/,BACKGROUND OF THE INVENTION The present invention relates to a process for the preparation of novel derivatives of 3-hydroxy-2-phenylpropionic acid of general formula I, -A-c, R 1, J 2, CHCOOCaH 5 (III),
HCOOHHCOOH
CH.,OH ve kterém R značí atom chloru, isopropylovounebo isobutylovou skupinu. Látky tohotoobecného vzorce jsou klíčovými meziproduktysyntézy esterů kyseliny 1-p-chlorbenzoyl-5--methoxy-2-methylr3-indolyloctové, kteréjsou významně . pro t.izáně 11 ivě účinné /čs.autorské osvědčení č. 195 614/.CH 3 OH in which R represents a chlorine atom, an isopropyl or isobutyl group. The compounds of this general formula are key intermediates in the synthesis of 1-p-chlorobenzoyl-5-methoxy-2-methyl-3-indolylacetic acid esters, which are significantly. for the purpose of the Act No. 195 614 /.
Podle vynálezu se nové deriváty obecnéhovzorce X připravují tak, že se na ethylesterkyseliny fenyloctové obecného vzorce II R '11Z ’According to the invention, the novel derivatives of general formula X are prepared by taking the ethyl esters of phenylacetic acid of the formula II R '11Z'
ve kterém R značí totéž co ve vzorci I, pů-sobí paraformaldehydem pro zavedení hydro-xymethylové skupiny do eC-polohy ke karbo-xylové skupině sloučeniny obecného vzorceII, za přítomnosti alkoholátu alkalickéhokovu, s výhodou ethylátu sodného, v pro-středí inertního organického rozpouštědla,například dimethylsulfoxidu, a vzniklýethylester obecného vzorce III ve kterém R značí totéž co ve vzorci I, sezmýdelní, například varem s ethanolickýmroztokem hydroxidu sodného. Výchozí ethylestery kyseliny fenylocto-vé obecného vzorce II jsou látky známé,které se připravují postupy známými z li-teratury.wherein R is the same as in Formula I, the paraformaldehyde for introducing the hydroxymethyl group into the e-position of the carboxyl group of Formula II, in the presence of an alcoholate of an alkali, preferably sodium ethylate, in an inert organic solvent for example dimethylsulfoxide and the resulting ethyl ester of formula III wherein R is the same as in formula I, for example by boiling with an ethanolic solution of sodium hydroxide. The starting ethyl esters of phenylacetic acid of formula (II) are those known to be prepared by procedures known in the art.
Bližší podrobnosti způsobu podle vynále-zu jsou patrny.z následujících příkladůprovedení, které tento způsob pouze ilustru-jí, ale nijak neomezují. Příklad!Further details of the process according to the invention can be seen in the following examples, which are merely illustrative but not limiting. Example!
Ke směsi 21 g p-chlorfenyloctanu ethylna-tého a 3,15 g paraformaldehydu ve .115 mlbezvodého dimethylsulfoxidu se za míchánípřidá 11,5 ml 0,5 M ethanolického roztokuethylátu sodného. V míchání se pokračuje30 minut, reakční směs se okyselí kyselinouoctovou, dimethylsulfoxid se oddestiluje zasníženého tlaku a destilací odparku se zís-ká 11,95 g čistého esteru, t. v. 125 až128 °C /66 Pa. Toto množství esteru se za-hřeje s ethanolickým roztokem hydroxidusodného, připraveným z 1,23 g sodíku, 37 mlethanolu a 1,43 ml vody, 5 minut k varua směs se nechá stát 3 hodiny při teplotěmístnosti. Vyloučená sůl kyseliny /4 g/' se 195615To a mixture of 21 g of ethyl-p-chlorophenylacetic acid and 3.15 g of paraformaldehyde in 115 ml of anhydrous dimethyl sulfoxide, 11.5 ml of 0.5 M ethanolic sodium ethylate solution are added with stirring. Stirring was continued for 30 minutes, the reaction was acidified with acetic acid, the dimethyl sulfoxide was distilled off under reduced pressure, and the residue was distilled to give 11.95 g of pure ester, mp 125-128 ° C / 66 Pa. This amount of ester is heated with ethanolic hydroxide solution prepared from 1.23 g of sodium, 37 ml of methanol and 1.43 ml of water, and boiled for 5 minutes at room temperature. Excluded acid salt (4 g / s) 195615
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS238578A CS195615B1 (en) | 1978-04-12 | 1978-04-12 | Method of producing derivatives of 3-hydroxy-2-phenylpropionic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS238578A CS195615B1 (en) | 1978-04-12 | 1978-04-12 | Method of producing derivatives of 3-hydroxy-2-phenylpropionic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS195615B1 true CS195615B1 (en) | 1980-02-29 |
Family
ID=5360846
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS238578A CS195615B1 (en) | 1978-04-12 | 1978-04-12 | Method of producing derivatives of 3-hydroxy-2-phenylpropionic acid |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS195615B1 (en) |
-
1978
- 1978-04-12 CS CS238578A patent/CS195615B1/en unknown
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