CS224979B1 - The production of pentacyclic lactam-esters - Google Patents
The production of pentacyclic lactam-esters Download PDFInfo
- Publication number
- CS224979B1 CS224979B1 CS571882A CS571882A CS224979B1 CS 224979 B1 CS224979 B1 CS 224979B1 CS 571882 A CS571882 A CS 571882A CS 571882 A CS571882 A CS 571882A CS 224979 B1 CS224979 B1 CS 224979B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- formula
- esters
- pentacyclic
- lactam
- production
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 claims description 14
- 238000009835 boiling Methods 0.000 claims description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 6
- -1 lactam esters Chemical class 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 4
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- DJURADWGRQFBAB-UHFFFAOYSA-N methyl 3-[3-(3-methoxy-3-oxopropyl)-2-oxocyclohexyl]propanoate Chemical compound COC(=O)CCC1CCCC(CCC(=O)OC)C1=O DJURADWGRQFBAB-UHFFFAOYSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 241000219289 Silene Species 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- ASGJEMPQQVNTGO-UHFFFAOYSA-N benzene chloroform Chemical compound C(Cl)(Cl)Cl.C1=CC=CC=C1.C1=CC=CC=C1 ASGJEMPQQVNTGO-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- MARBNQWAIKUQLO-UHFFFAOYSA-N methyl 3-[3-(3-methoxy-3-oxopropyl)-2-oxocyclopentyl]propanoate Chemical compound COC(=O)CCC1CCC(CCC(=O)OC)C1=O MARBNQWAIKUQLO-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Description
Vynález se týká způsobu výroby pentacyklických laktam-The present invention relates to a process for the preparation of pentacyclic lactams.
ve kterém R značí alkyl s 1 až 4 atomy uhlíku a n je 2 nebo 3. Sloučeniny vzorce I jsou vesměs nové a představují důležité me ziprodukty při výrobě biologicky aktivních látek.wherein R is C1-C4 alkyl and n is 2 or 3. The compounds of formula I are all novel and are important intermediates in the production of biologically active substances.
Podstata způsobu výroby podle vynálezu spočívá v tom, že se diestery 2-oxo-cykloalkan-1,3-dipropionových kyselin Obecné ho vzorce II,The process according to the invention is characterized in that the diesters of 2-oxo-cycloalkane-1,3-dipropionic acids of the general formula II,
ROOCROOC
COOR (II) ve kterém R i n mají shora uvedený význam, zahřívají k varu s tryptaminem vzorce IIICOOR (II) wherein R 1 and n are as defined above, are heated to boiling with the tryptamine of formula III
(III) ve výševroucím organickém rozpouštědle, jako např. v xylenu, diglymu, difenyletheru nebo chlorbenzenu.(III) in a high boiling organic solvent such as xylene, diglyme, diphenyl ether or chlorobenzene.
Následující příklady ilustrují, avšak nikterak neomezují obecnost způsobu výroby podle vynálezu.The following examples illustrate but do not limit the generality of the inventive process.
PřikladlHe did
224 979224 979
Směs 16^22 g (60 mmol) dimethyl-2-oxocyklohexan-1,3-dipropionátu (II ·,' R = CH^, n = 3) a 9^61 g (60 mmol) tryptaminu (III) se zahřívá k varu ve 150 ml silenu 11^5 h a koncentruje se ve vakuu vodní vývěvy. Zbytek se rozpustí v 500 ml chloroformu a promyje se postupně 100 ml 3% kyseliny chlorovodíkové, 100 ml vody a 50 ml solanky. Organická fáze se vysuší bezvodým síranem hořečnatým a zahustí se za sníženého tlaku. Odparek se chromatografuje na 130 g silikagelu. Odpařením benzen-chloroformových eluátů (3:1 až 1:1) na rotační vakuové odparce a následující krystalisací ze směsi methanolu a ethyl-acetátu se získá 7^78 g (34^1 %) laktamesteru vzorce I (R = GH^, n = 3). Teplota tání leží v rozmezí 148 až 149r5 °C.A mixture of 16 - 22 g (60 mmol) of dimethyl 2-oxocyclohexane-1,3-dipropionate (II, R = CH3, n = 3) and 9 - 61 g (60 mmol) of tryptamine (III) is heated to boiling in 150 ml of 11- 5 h silene and concentrated in a water pump vacuum. The residue was dissolved in 500 ml of chloroform and washed successively with 100 ml of 3% hydrochloric acid, 100 ml of water and 50 ml of brine. The organic phase was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue is chromatographed on 130 g of silica gel. Evaporation of the benzene-chloroform eluates (3: 1 to 1: 1) on a rotary evaporator followed by crystallization from a mixture of methanol and ethyl acetate gave 7 ^ 78 g (34 1 1%) of the lactamester of formula I (R = GH ^, n). = 3). The melting point ranges from 148 to 149 y 5 ° C.
Příklad 2Example 2
Směs 13^58 g (53 mmol) dimethyl-2-oxocyklopentan~1,3-dipropionátu (II, R = CH^, n = 2), 8^01 g (50 mmol) tryptaminu (III) a 170 ml diglymu se zahřívá k varu 9 h a odpaří se ve vakuu vodní vývěvy. Zbytek se chromatografuje na 115 g silikagelu. Eluáty směsí benzenu a chloroformu 4:1 až 1:1 se spojí a odpaří za sníženého tlaku na rotační odparce. Odparek se krystaluje z methanolu a získá se 8^16 g laktam-esteru vzorce I (R = CHp n = 2) s teplotou tání 124 až 127 °C · Výtěžek odpovídá 44^5 %· Příklad 3A mixture of 13-58 g (53 mmol) of dimethyl 2-oxocyclopentane-1,3-dipropionate (II, R = CH3, n = 2), 8.01 g (50 mmol) of tryptamine (III) and 170 ml of diglyme is added. Heat to boiling 9 h and evaporate in a water pump vacuum. The residue is chromatographed on 115 g of silica gel. The eluates of benzene / chloroform 4: 1 to 1: 1 were combined and evaporated under reduced pressure on a rotary evaporator. The residue is crystallized from methanol to give 8 16 g of the lactam ester of formula I (R = CHp n = 2), m.p. 124-127 ° C.
Postupem podle příkladu 2 se získá z dibutyl-2-oxocyklopentan-1,3-dipropionátu (II, R = CH3CH2CH2CH2, n = 2) 19,7 % laktamesteru vzorce I (R = CH3CH2CH2GH2, n = 2) v podobě transparentního skla.Following the procedure of Example 2, 19.7% of the lactamester of formula I (R = CH 3 CH 2 ) was obtained from dibutyl 2-oxocyclopentane-1,3-dipropionate (II, R = CH 3 CH 2 CH 2 CH 2 , n = 2). CH 2 GH 2 , n = 2) in the form of transparent glass.
Příklad 4Example 4
Postupem podle příkladu 1 se získá z dibutyl-2-oxocyklohexan1,3-dipropionátu (II, R = GH^CHgCHgCHg, n - 3) 22^8 % laktam-esteru vzorce I (R = CH^CHgCHgCHg, n = 3) v podobě transparentního skla.Following the procedure of Example 1, 22% -8% of the lactam ester of formula I (R = CH3CH3CHgCHg, n = 3) is obtained from dibutyl 2-oxocyclohexane-1,3-dipropionate (II, R = GH2CH2CHgCHg, n-3). form of transparent glass.
Směs 2,7 g (10 mmol) dimethyl-2-oxocyklohexan-1,3-dipropio nátu (II, R = CHp n = 3), 1,6 g (10 mmol)tryptaminu (III) a 50 ml chlorbenzenu se zahřívá 25 h k varu a zpracuje se podle příkladu 2. Získá se 30,7 % (1,17 g) laktam-esteru vzorce I (R = CH^, n = 3) s teplotou tání 148,5 až 149,5 °C.A mixture of 2.7 g (10 mmol) of dimethyl 2-oxocyclohexane-1,3-dipropionate (II, R = CHp n = 3), 1.6 g (10 mmol) of tryptamine (III) and 50 ml of chlorobenzene is heated. It was boiled for 25 h and worked up as in Example 2. 30.7% (1.17 g) of the lactam ester of formula I (R = CH 2, n = 3) were obtained, m.p. 148.5-149.5 ° C.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS571882A CS224979B1 (en) | 1982-07-29 | 1982-07-29 | The production of pentacyclic lactam-esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS571882A CS224979B1 (en) | 1982-07-29 | 1982-07-29 | The production of pentacyclic lactam-esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS224979B1 true CS224979B1 (en) | 1984-02-13 |
Family
ID=5402585
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS571882A CS224979B1 (en) | 1982-07-29 | 1982-07-29 | The production of pentacyclic lactam-esters |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS224979B1 (en) |
-
1982
- 1982-07-29 CS CS571882A patent/CS224979B1/en unknown
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