GB1432385A - 2-alkoxy- - Google Patents
2-alkoxy-Info
- Publication number
- GB1432385A GB1432385A GB3202373A GB3202373A GB1432385A GB 1432385 A GB1432385 A GB 1432385A GB 3202373 A GB3202373 A GB 3202373A GB 3202373 A GB3202373 A GB 3202373A GB 1432385 A GB1432385 A GB 1432385A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- compounds
- hydrogen
- protecting
- alkyl
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- -1 aluminium nitrile Chemical class 0.000 abstract 4
- 238000006243 chemical reaction Methods 0.000 abstract 4
- 150000002596 lactones Chemical class 0.000 abstract 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract 2
- 239000003513 alkali Substances 0.000 abstract 2
- 125000006239 protecting group Chemical group 0.000 abstract 2
- 150000000180 1,2-diols Chemical class 0.000 abstract 1
- WQADWIOXOXRPLN-UHFFFAOYSA-N 1,3-dithiane Chemical compound C1CSCSC1 WQADWIOXOXRPLN-UHFFFAOYSA-N 0.000 abstract 1
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 abstract 1
- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 abstract 1
- 101000653791 Bos taurus Protein S100-A12 Proteins 0.000 abstract 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 abstract 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 125000005037 alkyl phenyl group Chemical group 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 239000004411 aluminium Substances 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000003776 cleavage reaction Methods 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000000640 hydroxylating effect Effects 0.000 abstract 1
- 125000000468 ketone group Chemical group 0.000 abstract 1
- 229910052987 metal hydride Inorganic materials 0.000 abstract 1
- 150000004681 metal hydrides Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000006501 nitrophenyl group Chemical group 0.000 abstract 1
- 238000005949 ozonolysis reaction Methods 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 abstract 1
- 230000007017 scission Effects 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 1
- 229940070710 valerate Drugs 0.000 abstract 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
- C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1432385 2 - Alkoxy - cyclopenta[b]furan - 4- carboxaldehydes F HOFFMANN-LA ROCHE & CO AG 5 July 1973 [6 July 1972] 32023/73 Heading C2C Novel compounds I: in which R<SP>1</SP> is C 1-6 alkyl and R<SP>2</SP> is hydrogen or a protecting group are prepared from compounds II by (1) reaction with a dialkyl aluminium nitrile to give a compound III: and reducing the cyano group to formyl optionally after protecting the free hydroxyl group, (2) reaction with an alkali or alkaline earth metal salt of 1,3-dithian to give a compound IV: optionally protecting the free hydroxy and alkylating at least one of the S atoms followed by hydrolysis, or (3) reaction with MC#CR<SP>3</SP> in which R<SP>3</SP> is hydrogen, C 1-10 alkyl, C 3-7 cycloalkyl, C 2-10 alkenyl, phenyl, C 1-6 alkylphenyl, nitrophenyl or the group -C(OR<SP>6</SP>)R<SP>4</SP>R<SP>5</SP> (in which R<SP>4</SP> and R<SP>5</SP> are hydrogen or C 1-6 alkyl or R<SP>4</SP> and R<SP>8</SP> together with the C atom to which they are attached represent C 3-7 cycloalkyl and R<SP>6</SP> is hydrogen or a protecting group) and M is an alkali or alkaline earth metal to form a compound VII: optionally protecting the free hydroxy group, hydrogenating the acetylenic group to an olefine and either converting the double bond into a 1,2-diol followed by glucol cleavage or subjecting the double bond to ozonolysis. 3a#,6a#- Hexahydro - 5α - hydroxy - 2# - methoxy - 2H- cyclopenta[b]furan - 4# - carboxaldehyde is prepared. Compounds XIV: in which R<SP>9</SP> is hydrogen and R<SP>10</SP> is hydroxy or R<SP>9</SP> and R<SP>10</SP> together represent oxo and the dotted line is an optional bond, are prepared from compounds I by reaction with either (i) a phosphonate in which R<SP>8</SP> is C 1-6 alkyl and, if desired, reducing the keto group to hydroxyl by use of a complex metal hydride or (ii) a phosphonium compound in which X<SP>(-)</SP> is an anion of an acid. 3a#,6a#- Hexahydro - 2# - methoxy - 4# - [3 - (methoxymethoxy) - 1 - octenyl] - 2H - cyclopenta[b]furan- 5α-ol is reacted with sodium-5-(triphenylphosphonium)valerate to form a C 15 -epimeric mixture of racemic PGF 2α . Optically active derivatives of compounds XV: are prepared by reacting the racemic lactone with α-phenethylamine, separating the diasterisomeric amides and saponifying to yield the optically active lactones. The lactones are used to prepare compounds II by known procedures.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH768475A CH581644A5 (en) | 1972-07-06 | 1972-07-06 | |
| CH1012072A CH583219A5 (en) | 1972-07-06 | 1972-07-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1432385A true GB1432385A (en) | 1976-04-14 |
Family
ID=25701921
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2907375A Expired GB1432387A (en) | 1972-07-06 | 1973-07-05 | 2-alkoxy-4-m-dithian-2-yl-cyclopenta-b-furans |
| GB2907475A Expired GB1432388A (en) | 1972-07-06 | 1973-07-05 | 2-alkoxy-cyclopental-b-furans |
| GB3202373A Expired GB1432385A (en) | 1972-07-06 | 1973-07-05 | 2-alkoxy- |
| GB2907275A Expired GB1432386A (en) | 1972-07-06 | 1973-07-05 |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2907375A Expired GB1432387A (en) | 1972-07-06 | 1973-07-05 | 2-alkoxy-4-m-dithian-2-yl-cyclopenta-b-furans |
| GB2907475A Expired GB1432388A (en) | 1972-07-06 | 1973-07-05 | 2-alkoxy-cyclopental-b-furans |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2907275A Expired GB1432386A (en) | 1972-07-06 | 1973-07-05 |
Country Status (7)
| Country | Link |
|---|---|
| AT (1) | AT325599B (en) |
| BE (1) | BE801939A (en) |
| CH (2) | CH583219A5 (en) |
| DE (1) | DE2334275A1 (en) |
| FR (1) | FR2202886B1 (en) |
| GB (4) | GB1432387A (en) |
| NL (1) | NL7308866A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2599732B (en) | 2020-10-12 | 2023-05-17 | Cap Trac Ltd | Flooring element |
-
1972
- 1972-07-06 CH CH1012072A patent/CH583219A5/xx not_active IP Right Cessation
- 1972-07-06 CH CH768475A patent/CH581644A5/xx not_active IP Right Cessation
-
1973
- 1973-06-26 NL NL7308866A patent/NL7308866A/xx not_active Application Discontinuation
- 1973-07-04 FR FR7324552A patent/FR2202886B1/fr not_active Expired
- 1973-07-05 BE BE133137A patent/BE801939A/en unknown
- 1973-07-05 GB GB2907375A patent/GB1432387A/en not_active Expired
- 1973-07-05 GB GB2907475A patent/GB1432388A/en not_active Expired
- 1973-07-05 GB GB3202373A patent/GB1432385A/en not_active Expired
- 1973-07-05 AT AT592473A patent/AT325599B/en not_active IP Right Cessation
- 1973-07-05 DE DE19732334275 patent/DE2334275A1/en active Pending
- 1973-07-05 GB GB2907275A patent/GB1432386A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ATA592473A (en) | 1975-01-15 |
| DE2334275A1 (en) | 1974-01-24 |
| AT325599B (en) | 1975-10-27 |
| GB1432387A (en) | 1976-04-14 |
| NL7308866A (en) | 1974-01-08 |
| CH581644A5 (en) | 1976-11-15 |
| BE801939A (en) | 1974-01-07 |
| GB1432388A (en) | 1976-04-14 |
| FR2202886B1 (en) | 1978-07-21 |
| CH583219A5 (en) | 1976-12-31 |
| FR2202886A1 (en) | 1974-05-10 |
| GB1432386A (en) | 1976-04-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| 48S | Specification amended (sect. 8/1949) | ||
| 49R | Reference inserted (sect. 9/1949) | ||
| SPA | Amended specification published | ||
| PCNP | Patent ceased through non-payment of renewal fee |