IE42180L - Preparation of a-6-deoxytetracyclines - Google Patents
Preparation of a-6-deoxytetracyclinesInfo
- Publication number
- IE42180L IE42180L IE752514A IE251475A IE42180L IE 42180 L IE42180 L IE 42180L IE 752514 A IE752514 A IE 752514A IE 251475 A IE251475 A IE 251475A IE 42180 L IE42180 L IE 42180L
- Authority
- IE
- Ireland
- Prior art keywords
- hydrogenation
- preparation
- deoxytetracyclines
- ch609042a5
- methylenetetracycline
- Prior art date
Links
- 238000005984 hydrogenation reaction Methods 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 abstract 1
- 125000000068 chlorophenyl group Chemical group 0.000 abstract 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 abstract 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 abstract 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 abstract 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 238000011924 stereoselective hydrogenation Methods 0.000 abstract 1
- 125000003944 tolyl group Chemical group 0.000 abstract 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0073—Rhodium compounds
- C07F15/008—Rhodium compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/5045—Complexes or chelates of phosphines with metallic compounds or metals
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F41—WEAPONS
- F41A—FUNCTIONAL FEATURES OR DETAILS COMMON TO BOTH SMALLARMS AND ORDNANCE, e.g. CANNONS; MOUNTINGS FOR SMALLARMS OR ORDNANCE
- F41A9/00—Feeding or loading of ammunition; Magazines; Guiding means for the extracting of cartridges
- F41A9/01—Feeding of unbelted ammunition
- F41A9/24—Feeding of unbelted ammunition using a movable magazine or clip as feeding element
- F41A9/26—Feeding of unbelted ammunition using a movable magazine or clip as feeding element using a revolving drum magazine
- F41A9/27—Feeding of unbelted ammunition using a movable magazine or clip as feeding element using a revolving drum magazine in revolver-type guns
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F41—WEAPONS
- F41A—FUNCTIONAL FEATURES OR DETAILS COMMON TO BOTH SMALLARMS AND ORDNANCE, e.g. CANNONS; MOUNTINGS FOR SMALLARMS OR ORDNANCE
- F41A9/00—Feeding or loading of ammunition; Magazines; Guiding means for the extracting of cartridges
- F41A9/29—Feeding of belted ammunition
- F41A9/30—Sprocket-type belt transporters
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/60—Reduction reactions, e.g. hydrogenation
- B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
- B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
- B01J2231/645—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of C=C or C-C triple bonds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/822—Rhodium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- General Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The improved process applies to the preparation of a 6-deoxytetracycline by hydrogenation of a 6-deoxy-6-demethyl-6-methylenetetracycline. The process makes possible a stereoselective hydrogenation in favour of the alpha isomer, and it is characterised in that the hydrogenation is carried out at a temperature of 20 to 100 DEG C and at a pressure of 20 to 100 atmospheres, under practically neutral or slightly acidic conditions, in the presence of a catalyst of formula Rh(OCOR)2(P[C6H5]3) in which R = hydrogen, C1 to C6 alkyl, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, phenyl, chlorophenyl, tolyl or anisyl.
[CH609042A5]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53445274A | 1974-12-19 | 1974-12-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE42180L true IE42180L (en) | 1976-06-19 |
| IE42180B1 IE42180B1 (en) | 1980-06-18 |
Family
ID=24130096
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2514/75A IE42180B1 (en) | 1974-12-19 | 1975-11-18 | Preparation of -6-deoxytetracyclines |
Country Status (26)
| Country | Link |
|---|---|
| JP (1) | JPS5186457A (en) |
| AR (1) | AR208347A1 (en) |
| AT (1) | AT344320B (en) |
| AU (1) | AU476488B2 (en) |
| BE (1) | BE836775A (en) |
| BG (1) | BG24798A3 (en) |
| CH (1) | CH609042A5 (en) |
| CS (1) | CS203099B2 (en) |
| DD (1) | DD123600A5 (en) |
| DE (1) | DE2554564A1 (en) |
| DK (1) | DK151224C (en) |
| ES (1) | ES443626A1 (en) |
| FI (1) | FI59395C (en) |
| FR (1) | FR2295014A1 (en) |
| HU (1) | HU173508B (en) |
| IE (1) | IE42180B1 (en) |
| LU (1) | LU74054A1 (en) |
| NL (1) | NL164849B (en) |
| NO (1) | NO146236C (en) |
| PH (1) | PH13795A (en) |
| PL (1) | PL105946B1 (en) |
| RO (1) | RO72846A (en) |
| SE (1) | SE426587B (en) |
| SU (1) | SU799650A3 (en) |
| YU (1) | YU39474B (en) |
| ZA (1) | ZA757902B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE435619C (en) * | 1973-02-01 | 1985-10-31 | Pfizer | PROCEDURE FOR PREPARING A 6ALFA DEOXYTETRACYCLINE |
| DK386784A (en) * | 1983-08-17 | 1985-02-18 | Hovione Int Ltd | PROCEDURE FOR PREPARING ALFA-6-DESOXY-TETRACYCLINES |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1368431A (en) * | 1970-07-22 | 1974-09-25 | Johnson Matthey Co Ltd | Rhodium complex and methods of preparing the complex |
| SE435619C (en) * | 1973-02-01 | 1985-10-31 | Pfizer | PROCEDURE FOR PREPARING A 6ALFA DEOXYTETRACYCLINE |
-
1975
- 1975-01-01 AR AR261678A patent/AR208347A1/en active
- 1975-11-18 IE IE2514/75A patent/IE42180B1/en unknown
- 1975-11-20 SE SE7513091A patent/SE426587B/en not_active IP Right Cessation
- 1975-12-03 YU YU3050/75A patent/YU39474B/en unknown
- 1975-12-03 NO NO754085A patent/NO146236C/en unknown
- 1975-12-04 PH PH17832A patent/PH13795A/en unknown
- 1975-12-04 DE DE19752554564 patent/DE2554564A1/en active Pending
- 1975-12-09 FI FI753459A patent/FI59395C/en not_active IP Right Cessation
- 1975-12-10 AT AT937675A patent/AT344320B/en not_active IP Right Cessation
- 1975-12-12 JP JP50148315A patent/JPS5186457A/en active Granted
- 1975-12-17 CH CH1636475A patent/CH609042A5/en not_active IP Right Cessation
- 1975-12-17 PL PL1975185665A patent/PL105946B1/en unknown
- 1975-12-18 SU SU752198555A patent/SU799650A3/en active
- 1975-12-18 RO RO7584246A patent/RO72846A/en unknown
- 1975-12-18 ES ES443626A patent/ES443626A1/en not_active Expired
- 1975-12-18 LU LU74054A patent/LU74054A1/xx unknown
- 1975-12-18 AU AU87668/75A patent/AU476488B2/en not_active Expired
- 1975-12-18 ZA ZA00757902A patent/ZA757902B/en unknown
- 1975-12-18 HU HU74PI502A patent/HU173508B/en not_active IP Right Cessation
- 1975-12-18 BE BE1007088A patent/BE836775A/en not_active IP Right Cessation
- 1975-12-18 DK DK576575A patent/DK151224C/en not_active IP Right Cessation
- 1975-12-19 DD DD190359A patent/DD123600A5/xx unknown
- 1975-12-19 CS CS758721A patent/CS203099B2/en unknown
- 1975-12-19 FR FR7539084A patent/FR2295014A1/en active Granted
- 1975-12-19 BG BG7500031853A patent/BG24798A3/en unknown
- 1975-12-19 NL NL7514840.A patent/NL164849B/en not_active IP Right Cessation
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