GB1479965A – Cyclopropane carboxylic acid derivatives
– Google Patents
GB1479965A – Cyclopropane carboxylic acid derivatives
– Google Patents
Cyclopropane carboxylic acid derivatives
Info
Publication number
GB1479965A
GB1479965A
GB1901/77A
GB190177A
GB1479965A
GB 1479965 A
GB1479965 A
GB 1479965A
GB 1901/77 A
GB1901/77 A
GB 1901/77A
GB 190177 A
GB190177 A
GB 190177A
GB 1479965 A
GB1479965 A
GB 1479965A
Authority
GB
United Kingdom
Prior art keywords
ethyl
trans
phosphoranes
bromoethyl
alkyl
Prior art date
1973-07-09
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
Application number
GB1901/77A
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.)
Sandoz AG
Original Assignee
Sandoz AG
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.)
1973-07-09
Filing date
1974-07-08
Publication date
1977-07-13
1973-07-09
Priority claimed from CH995973A
external-priority
patent/CH599147A5/en
1974-07-08
Application filed by Sandoz AG
filed
Critical
Sandoz AG
1977-07-13
Publication of GB1479965A
publication
Critical
patent/GB1479965A/en
Status
Expired
legal-status
Critical
Current
Links
Espacenet
Global Dossier
Discuss
YMGUBTXCNDTFJI-UHFFFAOYSA-N
cyclopropanecarboxylic acid
Chemical class
OC(=O)C1CC1
YMGUBTXCNDTFJI-UHFFFAOYSA-N
0.000
title
abstract
2
-1
Phosphonium halides
Chemical class
0.000
abstract
3
125000000217
alkyl group
Chemical group
0.000
abstract
3
125000001495
ethyl group
Chemical group
[H]C([H])([H])C([H])([H])*
0.000
abstract
3
VBQCHPIMZGQLAZ-UHFFFAOYSA-N
phosphorane
Chemical class
[PH5]
VBQCHPIMZGQLAZ-UHFFFAOYSA-N
0.000
abstract
3
125000001797
benzyl group
Chemical group
[H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])*
0.000
abstract
2
125000002496
methyl group
Chemical group
[H]C([H])([H])*
0.000
abstract
2
KWGRBVOPPLSCSI-WPRPVWTQSA-N
(-)-ephedrine
Chemical compound
CN[C@@H](C)[C@H](O)C1=CC=CC=C1
KWGRBVOPPLSCSI-WPRPVWTQSA-N
0.000
abstract
1
GFHWNIPRYUSIOE-RFZPGFLSSA-N
(1r,2s)-2-(2-bromoethyl)cyclopropane-1-carboxylic acid
Chemical compound
OC(=O)[C@@H]1C[C@H]1CCBr
GFHWNIPRYUSIOE-RFZPGFLSSA-N
0.000
abstract
1
KWGRBVOPPLSCSI-PSASIEDQSA-N
(1s,2r)-2-(methylamino)-1-phenylpropan-1-ol
Chemical class
CN[C@H](C)[C@@H](O)C1=CC=CC=C1
KWGRBVOPPLSCSI-PSASIEDQSA-N
0.000
abstract
1
125000006376
(C3-C10) cycloalkyl group
Chemical group
0.000
abstract
1
IRGLYXLMMVZWCV-UHFFFAOYSA-N
2-bromoethyl cyclopropanecarboxylate
Chemical class
BrCCOC(=O)C1CC1
IRGLYXLMMVZWCV-UHFFFAOYSA-N
0.000
abstract
1
DMAYBPBPEUFIHJ-UHFFFAOYSA-N
4-bromobut-1-ene
Chemical compound
BrCCC=C
DMAYBPBPEUFIHJ-UHFFFAOYSA-N
0.000
abstract
1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N
7553-56-2
Chemical group
[I]
ZCYVEMRRCGMTRW-UHFFFAOYSA-N
0.000
abstract
1
WKBOTKDWSSQWDR-UHFFFAOYSA-N
Bromine atom
Chemical group
[Br]
WKBOTKDWSSQWDR-UHFFFAOYSA-N
0.000
abstract
1
RYGMFSIKBFXOCR-UHFFFAOYSA-N
Copper
Chemical compound
[Cu]
RYGMFSIKBFXOCR-UHFFFAOYSA-N
0.000
abstract
1
FEWJPZIEWOKRBE-UHFFFAOYSA-N
Tartaric Acid
Chemical compound
[H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O
FEWJPZIEWOKRBE-UHFFFAOYSA-N
0.000
abstract
1
239000002253
acid
Substances
0.000
abstract
1
150000007513
acids
Chemical class
0.000
abstract
1
125000003710
aryl alkyl group
Chemical group
0.000
abstract
1
GDTBXPJZTBHREO-UHFFFAOYSA-N
bromine
Chemical group
BrBr
GDTBXPJZTBHREO-UHFFFAOYSA-N
0.000
abstract
1
229910052794
bromium
Inorganic materials
0.000
abstract
1
150000001735
carboxylic acids
Chemical class
0.000
abstract
1
229910052801
chlorine
Inorganic materials
0.000
abstract
1
239000000460
chlorine
Substances
0.000
abstract
1
125000001309
chloro group
Chemical group
Cl*
0.000
abstract
1
150000001875
compounds
Chemical class
0.000
abstract
1
KWGRBVOPPLSCSI-UHFFFAOYSA-N
d-ephedrine
Natural products
CNC(C)C(O)C1=CC=CC=C1
KWGRBVOPPLSCSI-UHFFFAOYSA-N
0.000
abstract
1
230000032050
esterification
Effects
0.000
abstract
1
238000005886
esterification reaction
Methods
0.000
abstract
1
150000002148
esters
Chemical class
0.000
abstract
1
YVPJCJLMRRTDMQ-UHFFFAOYSA-N
ethyl diazoacetate
Chemical compound
CCOC(=O)C=[N+]=[N-]
YVPJCJLMRRTDMQ-UHFFFAOYSA-N
0.000
abstract
1
230000003301
hydrolyzing effect
Effects
0.000
abstract
1
229910052740
iodine
Chemical group
0.000
abstract
1
239000011630
iodine
Chemical group
0.000
abstract
1
125000001624
naphthyl group
Chemical group
0.000
abstract
1
125000001997
phenyl group
Chemical group
[H]C1=C([H])C([H])=C(*)C([H])=C1[H]
0.000
abstract
1
Classifications
C—CHEMISTRY; METALLURGY
C07—ORGANIC CHEMISTRY
C07D—HETEROCYCLIC COMPOUNDS
C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
C07D309/10—Oxygen atoms
C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
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
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
C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
C07F7/02—Silicon compounds
C07F7/08—Compounds having one or more C—Si linkages
C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
C07F7/1804—Compounds having Si-O-C linkages
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
Abstract
1479965 Phosphonium halides and phosphoranes SANDOZ Ltd 8 July 1974 [9 July 1973 4 May 1974] 01901/77 Divided out of 1479964 Headings C2P and C2C The invention comprises phosphonium halides and phosphoranes of the formulµ wherein R 1 is H, C 1-8 alkyl, C 3-10 cycloalkyl or C 7-12 aralkyl; R 2 is naphthyl or phenyl, each of which may be substituted by C 1-5 alkyl, or C 1-5 alkyl and X is chlorine, bromine or iodine and their preparation. The phosphoranes are obtained by reacting bases with the appropriate phosphonium halides, which are prepared by reacting the corresponding 2-(2-haloethyl)cyclopropanecarboxylic acids or esters thereof with compounds of the formula (B 2 ) 3 P. Methyl, ethyl and benzyl cis- and trans-()-2 (2 – bromoethyl)cyclopropanecarboxylates are prepared by esterifying the corresponding carboxylic acids, obtained by hydrolysing ethyl cis- and trans – () – 2 – (2 – bromo – ethyl)cyclopropanecarboxylates, which are made by reacting diazoacetic acid ethyl ester with 4-bromo-1- butene in the presence of copper powder at 100 C., and separating the isomeric products thus obtained trans-(r)-2-(2-bromoethyl)cyclopropanecarboxylic acid and trans – (-) – 2 – (2- bromoethyl)cyclopropanecarboxylic acid and resolving the racemic acid via the (-)-ephedrine and (+)-ephedrine salts respectively. The resolved acids are converted to the methyl, ethyl and benzyl esters by esterification.
GB1901/77A
1973-07-09
1974-07-08
Cyclopropane carboxylic acid derivatives
Expired
GB1479965A
(en)
Applications Claiming Priority (2)
Application Number
Priority Date
Filing Date
Title
CH995973A
CH599147A5
(en)
1973-07-09
1973-07-09
Long-acting synthetic prostaglandins
CH604974
1974-05-04
Publications (1)
Publication Number
Publication Date
GB1479965A
true
GB1479965A
(en)
1977-07-13
Family
ID=25698889
Family Applications (2)
Application Number
Title
Priority Date
Filing Date
GB1901/77A
Expired
GB1479965A
(en)
1973-07-09
1974-07-08
Cyclopropane carboxylic acid derivatives
GB30268/74A
Expired
GB1479964A
(en)
1973-07-09
1974-07-08
2,3-methylene prostaglandins and their preparation
Family Applications After (1)
Application Number
Title
Priority Date
Filing Date
GB30268/74A
Expired
GB1479964A
(en)
1973-07-09
1974-07-08
2,3-methylene prostaglandins and their preparation
Country Status (15)
Country
Link
JP
(1)
JPS5040549A
(en)
AT
(1)
AT355233B
(en)
CA
(1)
CA1050976A
(en)
DD
(1)
DD113348A5
(en)
DE
(1)
DE2431930A1
(en)
DK
(1)
DK142143B
(en)
ES
(2)
ES428063A1
(en)
FI
(1)
FI58117C
(en)
FR
(2)
FR2236490B1
(en)
GB
(2)
GB1479965A
(en)
IE
(1)
IE41342B1
(en)
IL
(1)
IL45215A
(en)
NL
(1)
NL7409119A
(en)
NO
(1)
NO742378L
(en)
SE
(2)
SE7408689L
(en)
Families Citing this family (5)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
DE2638401A1
(en)
*
1975-09-05
1977-03-17
Sandoz Ag
NEW PROSTAGLANDIN, THEIR USE AND MANUFACTURING
JPS52116930U
(en)
*
1976-03-03
1977-09-05
JPS55147056U
(en)
*
1979-04-06
1980-10-22
US4431669A
(en)
*
1982-12-17
1984-02-14
Schering Corporation
Cyclopropyl substituted polyenes
JPH04204679A
(en)
*
1990-11-30
1992-07-27
Fuji Photo Film Co Ltd
Electrophotographic image recorder
1974
1974-07-01
FI
FI2011/74A
patent/FI58117C/en
active
1974-07-01
DK
DK352974AA
patent/DK142143B/en
unknown
1974-07-01
NO
NO742378A
patent/NO742378L/no
unknown
1974-07-01
SE
SE7408689A
patent/SE7408689L/xx
unknown
1974-07-03
DE
DE2431930A
patent/DE2431930A1/en
not_active
Withdrawn
1974-07-05
NL
NL7409119A
patent/NL7409119A/en
not_active
Application Discontinuation
1974-07-05
DD
DD179745A
patent/DD113348A5/xx
unknown
1974-07-05
FR
FR7423427A
patent/FR2236490B1/fr
not_active
Expired
1974-07-08
GB
GB1901/77A
patent/GB1479965A/en
not_active
Expired
1974-07-08
CA
CA204,340A
patent/CA1050976A/en
not_active
Expired
1974-07-08
JP
JP49077462A
patent/JPS5040549A/ja
active
Pending
1974-07-08
AT
AT559874A
patent/AT355233B/en
not_active
IP Right Cessation
1974-07-08
IL
IL45215A
patent/IL45215A/en
unknown
1974-07-08
IE
IE1443/74A
patent/IE41342B1/en
unknown
1974-07-08
GB
GB30268/74A
patent/GB1479964A/en
not_active
Expired
1974-07-08
ES
ES74428063A
patent/ES428063A1/en
not_active
Expired
1975
1975-10-30
SE
SE7512194A
patent/SE7512194L/en
unknown
1976
1976-05-17
ES
ES448000A
patent/ES448000A1/en
not_active
Expired
1976-10-01
FR
FR7629555A
patent/FR2318169A1/en
active
Granted
Also Published As
Publication number
Publication date
NL7409119A
(en)
1975-01-13
IE41342B1
(en)
1979-12-05
IE41342L
(en)
1975-01-09
JPS5040549A
(en)
1975-04-14
SE7512194L
(en)
1975-10-30
CA1050976A
(en)
1979-03-20
GB1479964A
(en)
1977-07-13
ES428063A1
(en)
1977-02-01
ATA559874A
(en)
1979-07-15
DK142143C
(en)
1981-02-09
DD113348A5
(en)
1975-06-05
FR2236490B1
(en)
1978-07-21
FR2318169B1
(en)
1978-11-03
SE7408689L
(en)
1975-01-10
FI58117B
(en)
1980-08-29
NO742378L
(en)
1975-02-03
DK352974A
(en)
1975-03-03
AT355233B
(en)
1980-02-25
ES448000A1
(en)
1977-11-01
DE2431930A1
(en)
1975-01-30
IL45215A0
(en)
1975-02-10
FR2236490A1
(en)
1975-02-07
DK142143B
(en)
1980-09-08
FR2318169A1
(en)
1977-02-11
FI58117C
(en)
1980-12-10
FI201174A
(en)
1975-01-10
IL45215A
(en)
1977-07-31
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Legal Events
Date
Code
Title
Description
1977-11-23
PS
Patent sealed [section 19, patents act 1949]
1981-02-25
PCNP
Patent ceased through non-payment of renewal fee
