IE37562L - Preparation of 7-aminocephalosporanic acid - Google Patents
Preparation of 7-aminocephalosporanic acidInfo
- Publication number
- IE37562L IE37562L IE730646A IE64673A IE37562L IE 37562 L IE37562 L IE 37562L IE 730646 A IE730646 A IE 730646A IE 64673 A IE64673 A IE 64673A IE 37562 L IE37562 L IE 37562L
- Authority
- IE
- Ireland
- Prior art keywords
- amino
- group
- imino
- cephalosporin
- halide
- Prior art date
Links
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 title abstract 2
- -1 amino, carboxyl Chemical group 0.000 abstract 4
- 229930186147 Cephalosporin Natural products 0.000 abstract 3
- 229940124587 cephalosporin Drugs 0.000 abstract 3
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 abstract 2
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 abstract 2
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 150000001780 cephalosporins Chemical class 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 230000002140 halogenating effect Effects 0.000 abstract 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 abstract 2
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 abstract 2
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 abstract 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000000903 blocking effect Effects 0.000 abstract 1
- 150000003857 carboxamides Chemical class 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 238000003776 cleavage reaction Methods 0.000 abstract 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- 125000003396 thiol group Chemical group [H]S* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/18—7-Aminocephalosporanic or substituted 7-aminocephalosporanic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D499/21—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a nitrogen atom directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
-
- 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)
- Cephalosporin Compounds (AREA)
Abstract
1421199 Preparation of 7-amino cephalosporanic acid and derivatives ELI LILLY & CO 17 April 1973 [1 May 1972 (2)] 18391/73 Heading C2C In a process for cleaving a 7-carboxamido group of a cephalosporin to produce the corresponding 7-amino cephalosporin wherein any amino, carboxyl, hydroxy and mercapto group is blocked with a blocking reagent and wherein the blocked cephalosporin is treated with an halogenating agent to convert the 7-carboxamido group to an imino halide, the imino halide is treated with an alcohol to form an imino ether and the imino ether is hydrolysed to a 7-amino group, the invention comprises conducting the carboxyl group protecting reaction and/or the carboxamide cleavage reactions in tetrahydrofuran, bis-(2-methoxyethyl)ether, 2- methoxyethyl acetate, ethylene glycol diacetate, 1,4-dioxane, or 1,3-dioxane, or mixtures thereof. In a modification, a catalytic amount of quinoline, isoquinoline, 3-picoline, 4-picoline, or pyridine or an acid addition salt thereof or a complex of such organic base with a C 2 to C 3 alkanoyl halide is added to the reaction mixture prior to the addition of the halogenating agent, to increase the yield.
[GB1421199A]
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US249293A US3904615A (en) | 1972-05-01 | 1972-05-01 | Process for cleaving cephalosporin compounds |
| US00249294A US3840532A (en) | 1972-05-01 | 1972-05-01 | Process for cleaving cephalosporin compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE37562L true IE37562L (en) | 1973-11-01 |
| IE37562B1 IE37562B1 (en) | 1977-08-17 |
Family
ID=26939961
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE646/73A IE37562B1 (en) | 1972-05-01 | 1973-04-25 | Process for preparing a cephalosporin |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS5842194B2 (en) |
| AR (1) | AR203623A1 (en) |
| CH (1) | CH582184A5 (en) |
| DD (1) | DD105239A5 (en) |
| DE (1) | DE2321234A1 (en) |
| ES (1) | ES414153A1 (en) |
| FR (1) | FR2183098B1 (en) |
| GB (1) | GB1421199A (en) |
| HU (2) | HU167444B (en) |
| IE (1) | IE37562B1 (en) |
| IL (1) | IL42087A (en) |
| NL (1) | NL181197C (en) |
| RO (1) | RO62896A (en) |
| SE (1) | SE418746B (en) |
| SU (1) | SU587867A3 (en) |
| YU (1) | YU108273A (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5256823U (en) * | 1975-10-22 | 1977-04-25 | ||
| DE2933075C2 (en) * | 1979-08-16 | 1984-04-19 | Zahnraederfabrik Renk Ag, 8900 Augsburg | Drive and brake systems for motor vehicles |
| JPH0633990U (en) * | 1992-09-29 | 1994-05-06 | 呉羽合繊株式会社 | Coloring device |
| JP3487083B2 (en) | 1996-02-09 | 2004-01-13 | 日立化成工業株式会社 | Thermosetting resin composition and cured product thereof |
| DE69840475D1 (en) * | 1997-06-04 | 2009-03-05 | Sandoz Ag | IMPROVED FILLING PROCESS OF 7-AMINOCEPHALOSPORAN ACID |
| US6518420B2 (en) | 1997-06-04 | 2003-02-11 | Biochemie Gesellschaft M.B.H. | Precipitation process of 7-aminocephalosporanic acid (7-ACA) |
| CN110094151B (en) * | 2018-01-31 | 2020-06-16 | 光宝电子(广州)有限公司 | Shutter |
-
1973
- 1973-03-27 ES ES414153A patent/ES414153A1/en not_active Expired
- 1973-04-17 GB GB1839173A patent/GB1421199A/en not_active Expired
- 1973-04-20 YU YU01082/73A patent/YU108273A/en unknown
- 1973-04-20 IL IL42087A patent/IL42087A/en unknown
- 1973-04-25 IE IE646/73A patent/IE37562B1/en unknown
- 1973-04-26 HU HUEI541A patent/HU167444B/hu unknown
- 1973-04-26 SE SE7305862A patent/SE418746B/en unknown
- 1973-04-26 DE DE2321234A patent/DE2321234A1/en not_active Ceased
- 1973-04-26 HU HUEI472A patent/HU167595B/hu unknown
- 1973-04-27 FR FR7315533A patent/FR2183098B1/fr not_active Expired
- 1973-04-28 SU SU731914796A patent/SU587867A3/en active
- 1973-04-30 CH CH612873A patent/CH582184A5/xx not_active IP Right Cessation
- 1973-05-01 NL NLAANVRAGE7306068,A patent/NL181197C/en active Search and Examination
- 1973-05-01 JP JP48047638A patent/JPS5842194B2/en not_active Expired
- 1973-05-02 RO RO7300074662A patent/RO62896A/en unknown
- 1973-05-02 DD DD170570A patent/DD105239A5/xx unknown
- 1973-10-26 AR AR250738A patent/AR203623A1/en active
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5842194B2 (en) | 1983-09-17 |
| AR203623A1 (en) | 1975-09-30 |
| DE2321234A1 (en) | 1973-11-22 |
| JPS4947387A (en) | 1974-05-08 |
| CH582184A5 (en) | 1976-11-30 |
| AU5468973A (en) | 1974-10-24 |
| HU167595B (en) | 1975-11-28 |
| ES414153A1 (en) | 1976-06-01 |
| RO62896A (en) | 1978-03-15 |
| SE418746B (en) | 1981-06-22 |
| YU108273A (en) | 1982-02-28 |
| NL7306068A (en) | 1973-11-05 |
| HU167444B (en) | 1975-10-28 |
| IL42087A0 (en) | 1973-06-29 |
| DD105239A5 (en) | 1974-04-12 |
| GB1421199A (en) | 1976-01-14 |
| FR2183098B1 (en) | 1975-08-22 |
| FR2183098A1 (en) | 1973-12-14 |
| IE37562B1 (en) | 1977-08-17 |
| SU587867A3 (en) | 1978-01-05 |
| IL42087A (en) | 1976-01-30 |
| NL181197C (en) | 1987-07-01 |
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