DE1931097C3 - Verfahren zur Herstellung von 6-Isocyana to- penicillansäure derivaten - Google Patents
Verfahren zur Herstellung von 6-Isocyana to- penicillansäure derivatenInfo
- Publication number
- DE1931097C3 DE1931097C3 DE1931097A DE1931097A DE1931097C3 DE 1931097 C3 DE1931097 C3 DE 1931097C3 DE 1931097 A DE1931097 A DE 1931097A DE 1931097 A DE1931097 A DE 1931097A DE 1931097 C3 DE1931097 C3 DE 1931097C3
- Authority
- DE
- Germany
- Prior art keywords
- toluene
- acid
- ester
- group
- penicillanic acid
- 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
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 7
- 230000008569 process Effects 0.000 title claims description 4
- RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical class OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 title description 4
- 239000002253 acid Substances 0.000 claims description 10
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 69
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- -1 phenacyl group Chemical group 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000002329 infrared spectrum Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 229930182555 Penicillin Natural products 0.000 description 2
- XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 2
- 229940077388 benzenesulfonate Drugs 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002960 penicillins Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000005051 trimethylchlorosilane Substances 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000005103 alkyl silyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- MTMNJFGEKOYMIV-UHFFFAOYSA-N carbonyl dichloride;toluene Chemical compound ClC(Cl)=O.CC1=CC=CC=C1 MTMNJFGEKOYMIV-UHFFFAOYSA-N 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- YGZSVWMBUCGDCV-UHFFFAOYSA-N chloro(methyl)silane Chemical compound C[SiH2]Cl YGZSVWMBUCGDCV-UHFFFAOYSA-N 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052736 halogen Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012430 organic reaction media Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL686808622A NL155260B (nl) | 1968-06-19 | 1968-06-19 | Werkwijze voor de bereiding van derivaten van 6-aminopenicillaanzuur. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1931097A1 DE1931097A1 (de) | 1970-01-02 |
| DE1931097B2 DE1931097B2 (de) | 1974-08-08 |
| DE1931097C3 true DE1931097C3 (de) | 1975-05-07 |
Family
ID=19803934
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1931097A Expired DE1931097C3 (de) | 1968-06-19 | 1969-06-19 | Verfahren zur Herstellung von 6-Isocyana to- penicillansäure derivaten |
Country Status (15)
| Country | Link |
|---|---|
| AT (2) | AT300194B (xx) |
| BE (1) | BE734708A (xx) |
| BR (1) | BR6909873D0 (xx) |
| CA (1) | CA922705A (xx) |
| CH (2) | CH547308A (xx) |
| DE (1) | DE1931097C3 (xx) |
| ES (1) | ES368569A1 (xx) |
| FR (1) | FR2011238B1 (xx) |
| GB (1) | GB1268536A (xx) |
| IE (1) | IE32890B1 (xx) |
| IL (1) | IL32329A (xx) |
| LU (1) | LU58901A1 (xx) |
| NL (1) | NL155260B (xx) |
| SE (1) | SE377126B (xx) |
| ZA (1) | ZA694354B (xx) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CS165353B2 (xx) * | 1969-12-18 | 1975-12-22 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE603703A (fr) * | 1960-07-05 | 1961-09-01 | Novo Terapeutisk Labor As | Dérivés de l'acide 6-amino-pénicillanique et leur procédé de préparation |
-
1968
- 1968-06-19 NL NL686808622A patent/NL155260B/xx unknown
-
1969
- 1969-06-02 IL IL32329A patent/IL32329A/xx unknown
- 1969-06-13 SE SE6908458A patent/SE377126B/xx unknown
- 1969-06-17 CH CH1324271A patent/CH547308A/xx not_active IP Right Cessation
- 1969-06-17 BE BE734708D patent/BE734708A/xx unknown
- 1969-06-17 CH CH923669A patent/CH528539A/de not_active IP Right Cessation
- 1969-06-18 AT AT658470A patent/AT300194B/de not_active IP Right Cessation
- 1969-06-18 BR BR209873/69A patent/BR6909873D0/pt unknown
- 1969-06-18 IE IE834/69A patent/IE32890B1/xx unknown
- 1969-06-18 LU LU58901D patent/LU58901A1/xx unknown
- 1969-06-18 ZA ZA694354A patent/ZA694354B/xx unknown
- 1969-06-18 AT AT575569A patent/AT290726B/de not_active IP Right Cessation
- 1969-06-18 GB GB30958/69A patent/GB1268536A/en not_active Expired
- 1969-06-19 CA CA054776A patent/CA922705A/en not_active Expired
- 1969-06-19 FR FR696920550A patent/FR2011238B1/fr not_active Expired
- 1969-06-19 DE DE1931097A patent/DE1931097C3/de not_active Expired
- 1969-06-19 ES ES368569A patent/ES368569A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BR6909873D0 (pt) | 1973-02-08 |
| IE32890L (en) | 1969-12-19 |
| NL6808622A (xx) | 1969-12-23 |
| ES368569A1 (es) | 1971-05-01 |
| IL32329A0 (en) | 1969-08-27 |
| BE734708A (xx) | 1969-12-17 |
| DE1931097B2 (de) | 1974-08-08 |
| AT290726B (de) | 1971-06-11 |
| LU58901A1 (xx) | 1969-11-12 |
| ZA694354B (en) | 1971-01-27 |
| DE1966702A1 (de) | 1973-09-06 |
| DE1931097A1 (de) | 1970-01-02 |
| CA922705A (en) | 1973-03-13 |
| FR2011238B1 (xx) | 1973-01-12 |
| IL32329A (en) | 1974-01-14 |
| NL155260B (nl) | 1977-12-15 |
| CH528539A (de) | 1972-09-30 |
| FR2011238A1 (xx) | 1970-02-27 |
| AT300194B (de) | 1972-07-10 |
| GB1268536A (en) | 1972-03-29 |
| SE377126B (xx) | 1975-06-23 |
| IE32890B1 (en) | 1974-01-09 |
| DE1966702B2 (de) | 1976-01-15 |
| CH547308A (de) | 1974-03-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |