IL43992A - Racemic 13beta-ethyl-3-methoxy-8,14-seco-gona-1,3,5(10),8-tetraene-17beta-ol-14-one and a process for the preparation thereof - Google Patents
Racemic 13beta-ethyl-3-methoxy-8,14-seco-gona-1,3,5(10),8-tetraene-17beta-ol-14-one and a process for the preparation thereofInfo
- Publication number
- IL43992A IL43992A IL43992A IL4399274A IL43992A IL 43992 A IL43992 A IL 43992A IL 43992 A IL43992 A IL 43992A IL 4399274 A IL4399274 A IL 4399274A IL 43992 A IL43992 A IL 43992A
- Authority
- IL
- Israel
- Prior art keywords
- ethyl
- gona
- methoxy
- tetraene
- seco
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 8
- 239000000203 mixture Substances 0.000 claims description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 11
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 7
- 239000012279 sodium borohydride Substances 0.000 claims description 7
- OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O OSVMTWJCGUFAOD-KZQROQTASA-N 0.000 claims description 6
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 125000004043 oxo group Chemical group O=* 0.000 claims description 5
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000000397 acetylating effect Effects 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000006257 total synthesis reaction Methods 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- FGVNCNTVSHHPTI-UHFFFAOYSA-N butoxyaluminum Chemical compound CCCCO[Al] FGVNCNTVSHHPTI-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000003803 gonane derivatives Chemical class 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 125000003198 secondary alcohol group Chemical group 0.000 description 1
- 150000003338 secosteroids Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 150000003431 steroids Chemical group 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUGO1230A HU170147B (en)) | 1973-01-31 | 1973-01-31 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL43992A0 IL43992A0 (en) | 1974-05-16 |
| IL43992A true IL43992A (en) | 1977-07-31 |
Family
ID=10996741
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL43992A IL43992A (en) | 1973-01-31 | 1974-01-10 | Racemic 13beta-ethyl-3-methoxy-8,14-seco-gona-1,3,5(10),8-tetraene-17beta-ol-14-one and a process for the preparation thereof |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS5641610B2 (en)) |
| AT (1) | AT346505B (en)) |
| BE (1) | BE810381A (en)) |
| BG (1) | BG23904A3 (en)) |
| CS (1) | CS165309B2 (en)) |
| DE (1) | DE2403985C2 (en)) |
| DK (1) | DK138314B (en)) |
| ES (1) | ES422607A1 (en)) |
| FR (1) | FR2216275B1 (en)) |
| GB (1) | GB1420892A (en)) |
| HU (1) | HU170147B (en)) |
| IL (1) | IL43992A (en)) |
| IT (1) | IT1043869B (en)) |
| NL (1) | NL7401256A (en)) |
| RO (1) | RO67880A (en)) |
| SE (1) | SE400977B (en)) |
| SU (1) | SU561515A3 (en)) |
| YU (1) | YU35750B (en)) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE541389C2 (en) * | 2017-12-20 | 2019-09-10 | Scania Cv Ab | System and Method for Controlling a Motor Vehicle to Drive Autonomously |
| SE541390C2 (en) * | 2017-12-20 | 2019-09-10 | Scania Cv Ab | System and Method for Controlling a Motor Vehicle to Drive Autonomously |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3549673A (en) * | 1967-03-09 | 1970-12-22 | Takeda Chemical Industries Ltd | Total synthesis of 13beta-substituted gonapolyen-17alpha-ols |
-
1973
- 1973-01-31 HU HUGO1230A patent/HU170147B/hu unknown
-
1974
- 1974-01-10 IL IL43992A patent/IL43992A/en unknown
- 1974-01-14 YU YU103/74A patent/YU35750B/xx unknown
- 1974-01-14 GB GB162874A patent/GB1420892A/en not_active Expired
- 1974-01-17 AT AT38374A patent/AT346505B/de not_active IP Right Cessation
- 1974-01-19 RO RO7477336A patent/RO67880A/ro unknown
- 1974-01-22 BG BG025563A patent/BG23904A3/xx unknown
- 1974-01-25 IT IT19776/74A patent/IT1043869B/it active
- 1974-01-25 ES ES422607A patent/ES422607A1/es not_active Expired
- 1974-01-25 CS CS491A patent/CS165309B2/cs unknown
- 1974-01-28 FR FR7402683A patent/FR2216275B1/fr not_active Expired
- 1974-01-29 JP JP1154774A patent/JPS5641610B2/ja not_active Expired
- 1974-01-29 SE SE7401140A patent/SE400977B/xx not_active IP Right Cessation
- 1974-01-29 DE DE2403985A patent/DE2403985C2/de not_active Expired
- 1974-01-30 BE BE140361A patent/BE810381A/xx not_active IP Right Cessation
- 1974-01-30 SU SU1991803A patent/SU561515A3/ru active
- 1974-01-30 NL NL7401256A patent/NL7401256A/xx not_active Application Discontinuation
- 1974-01-30 DK DK48374AA patent/DK138314B/da not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2403985C2 (de) | 1984-03-01 |
| FR2216275A1 (en)) | 1974-08-30 |
| YU35750B (en) | 1981-06-30 |
| DK138314B (da) | 1978-08-14 |
| HU170147B (en)) | 1977-04-28 |
| SU561515A3 (ru) | 1977-06-05 |
| SE400977B (sv) | 1978-04-17 |
| FR2216275B1 (en)) | 1977-09-23 |
| NL7401256A (en)) | 1974-08-02 |
| AT346505B (de) | 1978-11-10 |
| JPS5641610B2 (en)) | 1981-09-29 |
| IL43992A0 (en) | 1974-05-16 |
| BE810381A (en)) | 1974-05-16 |
| CS165309B2 (en)) | 1975-12-22 |
| BG23904A3 (en) | 1977-11-10 |
| GB1420892A (en) | 1976-01-14 |
| YU10374A (en) | 1980-10-31 |
| DE2403985A1 (de) | 1974-08-08 |
| ATA38374A (de) | 1978-03-15 |
| ES422607A1 (es) | 1977-04-16 |
| RO67880A (ro) | 1980-12-30 |
| DK138314C (en)) | 1979-02-05 |
| JPS5046653A (en)) | 1975-04-25 |
| IT1043869B (it) | 1980-02-29 |
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