FR2295014A1 - 6-Deoxy-6-demethyl 6-methylene-tetracycline hydrogenation - using dicarboxylato triphenylphosphine rhodium (II) complex as catalyst for stereospecificity (BE180676) - Google Patents

6-Deoxy-6-demethyl 6-methylene-tetracycline hydrogenation - using dicarboxylato triphenylphosphine rhodium (II) complex as catalyst for stereospecificity (BE180676)

Info

Publication number
FR2295014A1
FR2295014A1 FR7539084A FR7539084A FR2295014A1 FR 2295014 A1 FR2295014 A1 FR 2295014A1 FR 7539084 A FR7539084 A FR 7539084A FR 7539084 A FR7539084 A FR 7539084A FR 2295014 A1 FR2295014 A1 FR 2295014A1
Authority
FR
France
Prior art keywords
methylene
isomer
demethyl
deoxy
tetracycline
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.)
Granted
Application number
FR7539084A
Other languages
French (fr)
Other versions
FR2295014B1 (en
Inventor
Hermann Faubl
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Pfizer Inc
Original Assignee
Pfizer Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Pfizer Inc filed Critical Pfizer Inc
Publication of FR2295014A1 publication Critical patent/FR2295014A1/en
Application granted granted Critical
Publication of FR2295014B1 publication Critical patent/FR2295014B1/fr
Granted legal-status Critical Current

Links

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)
  • General Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (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

Hydrogenation of the exocyclic methylene gp. of a 6-deoxy-6-demethyl-6-methylene-tetracycline (I), or its acid addition salt, in a stereoselective manner giving the alpha-isomer in preference to the beta-isomer, is carried out at 20-100 degrees C and 1-100 atmos. under neutral conditions, or using a weakly acidic acid addn. salt, in the presence of a catalytic amt. of a cpd. of formula Rh(OCOR)2(P C6H5 3) (II) (where R = H, 1-6C alkyl, ClCH2, Cl2CH, Cl3C, FCH2, F2CH, F3C, phenyl, chlorphenyl, tolyl, anisyl). The ratio of alpha-isomer to beta-isomer is >=9:1. Known methods give a less favourable ratio e.g. 1:1.
FR7539084A 1974-12-19 1975-12-19 6-Deoxy-6-demethyl 6-methylene-tetracycline hydrogenation - using dicarboxylato triphenylphosphine rhodium (II) complex as catalyst for stereospecificity (BE180676) Granted FR2295014A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US53445274A 1974-12-19 1974-12-19

Publications (2)

Publication Number Publication Date
FR2295014A1 true FR2295014A1 (en) 1976-07-16
FR2295014B1 FR2295014B1 (en) 1978-10-06

Family

ID=24130096

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7539084A Granted FR2295014A1 (en) 1974-12-19 1975-12-19 6-Deoxy-6-demethyl 6-methylene-tetracycline hydrogenation - using dicarboxylato triphenylphosphine rhodium (II) complex as catalyst for stereospecificity (BE180676)

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)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2550788A1 (en) * 1983-08-17 1985-02-22 Hovione Int Ltd NEW PROCESS FOR THE PREPARATION OF A-6-DESOXYTETRACYCLINES

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE435619C (en) * 1973-02-01 1985-11-18 Pfizer PROCEDURE FOR PREPARING A 6ALFA DEOXYTETRACYCLINE

Family Cites Families (2)

* Cited by examiner, † Cited by third party
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 1985-11-18 Pfizer PROCEDURE FOR PREPARING A 6ALFA DEOXYTETRACYCLINE

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
NEANT *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2550788A1 (en) * 1983-08-17 1985-02-22 Hovione Int Ltd NEW PROCESS FOR THE PREPARATION OF A-6-DESOXYTETRACYCLINES
EP0137661A2 (en) * 1983-08-17 1985-04-17 Hovione Inter Ltd. A new process for the preparation of alpha-6-deoxy-tetracyclines
EP0137661A3 (en) * 1983-08-17 1987-08-19 Hovione Inter Ltd. A new process for the preparation of alpha-6-deoxy-tetracyclines

Also Published As

Publication number Publication date
RO72846A (en) 1982-04-12
AU476488B2 (en) 1976-09-23
DK151224B (en) 1987-11-16
BE836775A (en) 1976-06-18
CH609042A5 (en) 1979-02-15
NL164849B (en) 1980-09-15
NO754085L (en) 1976-06-22
NO146236C (en) 1982-08-25
FI753459A (en) 1976-06-20
AU8766875A (en) 1976-09-23
ZA757902B (en) 1976-12-29
ATA937675A (en) 1977-11-15
YU39474B (en) 1984-12-31
PH13795A (en) 1980-10-01
SU799650A3 (en) 1981-01-23
DK576575A (en) 1976-06-20
SE7513091L (en) 1976-06-21
FI59395C (en) 1981-08-10
FI59395B (en) 1981-04-30
NL7514840A (en) 1976-06-22
JPS5186457A (en) 1976-07-29
HU173508B (en) 1979-05-28
CS203099B2 (en) 1981-02-27
FR2295014B1 (en) 1978-10-06
AT344320B (en) 1978-07-10
YU305075A (en) 1982-05-31
DK151224C (en) 1988-05-16
DE2554564A1 (en) 1976-07-01
LU74054A1 (en) 1976-11-11
IE42180L (en) 1976-06-19
NO146236B (en) 1982-05-18
AR208347A1 (en) 1976-12-20
PL105946B1 (en) 1979-11-30
JPS5324944B2 (en) 1978-07-24
DD123600A5 (en) 1977-01-05
SE426587B (en) 1983-01-31
IE42180B1 (en) 1980-06-18
BG24798A3 (en) 1978-05-12
ES443626A1 (en) 1977-05-01

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