DE2942606A1 - Verfahren zur herstellung von saeureamiden und anwendung des verfahrens - Google Patents
Verfahren zur herstellung von saeureamiden und anwendung des verfahrensInfo
- Publication number
- DE2942606A1 DE2942606A1 DE19792942606 DE2942606A DE2942606A1 DE 2942606 A1 DE2942606 A1 DE 2942606A1 DE 19792942606 DE19792942606 DE 19792942606 DE 2942606 A DE2942606 A DE 2942606A DE 2942606 A1 DE2942606 A1 DE 2942606A1
- Authority
- DE
- Germany
- Prior art keywords
- isonitrile
- acid
- acid amides
- ome
- heteroatom
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 30
- 150000001408 amides Chemical class 0.000 title claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 title description 4
- 150000002527 isonitriles Chemical class 0.000 claims abstract description 26
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 8
- 150000001412 amines Chemical class 0.000 claims abstract description 7
- XFXPMWWXUTWYJX-UHFFFAOYSA-N isonitrile group Chemical group N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 3
- MFRZPLYKVDHOSN-UHFFFAOYSA-N 4-(2-isocyanoethyl)morpholine Chemical compound [C-]#[N+]CCN1CCOCC1 MFRZPLYKVDHOSN-UHFFFAOYSA-N 0.000 claims abstract 2
- 230000009435 amidation Effects 0.000 claims description 4
- 238000007112 amidation reaction Methods 0.000 claims description 4
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 claims description 3
- 238000010647 peptide synthesis reaction Methods 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229930186147 Cephalosporin Natural products 0.000 claims 1
- 229940124587 cephalosporin Drugs 0.000 claims 1
- 150000001780 cephalosporins Chemical class 0.000 claims 1
- 238000009736 wetting Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 125000001424 substituent group Chemical group 0.000 abstract description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 150000001718 carbodiimides Chemical class 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 102000004196 processed proteins & peptides Human genes 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000001413 amino acids Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000003948 formamides Chemical class 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- FRIISBOVHKVDFX-LURJTMIESA-N (2s)-2-[[2-[(2-methylpropan-2-yl)oxycarbonylamino]acetyl]amino]propanoic acid Chemical compound OC(=O)[C@H](C)NC(=O)CNC(=O)OC(C)(C)C FRIISBOVHKVDFX-LURJTMIESA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000011938 amidation process Methods 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 238000010640 amide synthesis reaction Methods 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- SIHNOQQFBTTYLO-YJBOKZPZSA-N methyl (2s)-3-phenyl-2-[[(2s)-2-(phenylmethoxycarbonylamino)propanoyl]amino]propanoate Chemical compound C([C@@H](C(=O)OC)NC(=O)[C@H](C)NC(=O)OCC=1C=CC=CC=1)C1=CC=CC=C1 SIHNOQQFBTTYLO-YJBOKZPZSA-N 0.000 description 1
- VYDUMGJTJHWTQL-UHFFFAOYSA-N methyl 2-methyl-2-[[2-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]propanoate Chemical compound COC(=O)C(C)(C)NC(=O)C(C)(C)NC(=O)OC(C)(C)C VYDUMGJTJHWTQL-UHFFFAOYSA-N 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- MMVGWKHDLPGACU-UHFFFAOYSA-N n-(2-morpholin-4-ylethyl)formamide Chemical compound O=CNCCN1CCOCC1 MMVGWKHDLPGACU-UHFFFAOYSA-N 0.000 description 1
- LKQUCICFTHBFAL-UHFFFAOYSA-N n-benzylbenzamide Chemical compound C=1C=CC=CC=1C(=O)NCC1=CC=CC=C1 LKQUCICFTHBFAL-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19792942606 DE2942606A1 (de) | 1979-10-22 | 1979-10-22 | Verfahren zur herstellung von saeureamiden und anwendung des verfahrens |
AT80106416T ATE8499T1 (de) | 1979-10-22 | 1980-10-21 | Verfahren zur herstellung von saeureamiden, verwendung des verfahrens und morpholino-aethylisocyanid. |
DE8080106416T DE3068616D1 (en) | 1979-10-22 | 1980-10-21 | Process for the preparation of acid amides, use of the process and morpholino-ethyl isocyanide |
EP80106416A EP0029909B1 (de) | 1979-10-22 | 1980-10-21 | Verfahren zur Herstellung von Säureamiden, Verwendung des Verfahrens und Morpholino-äthyl-isocyanid |
JP14699280A JPS5665851A (en) | 1979-10-22 | 1980-10-22 | Manufacture of acid amide |
US06/460,881 US4442029A (en) | 1979-10-22 | 1983-01-25 | Process for the preparation of acid amides and application of the process |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19792942606 DE2942606A1 (de) | 1979-10-22 | 1979-10-22 | Verfahren zur herstellung von saeureamiden und anwendung des verfahrens |
Publications (1)
Publication Number | Publication Date |
---|---|
DE2942606A1 true DE2942606A1 (de) | 1981-04-30 |
Family
ID=6084058
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19792942606 Withdrawn DE2942606A1 (de) | 1979-10-22 | 1979-10-22 | Verfahren zur herstellung von saeureamiden und anwendung des verfahrens |
DE8080106416T Expired DE3068616D1 (en) | 1979-10-22 | 1980-10-21 | Process for the preparation of acid amides, use of the process and morpholino-ethyl isocyanide |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE8080106416T Expired DE3068616D1 (en) | 1979-10-22 | 1980-10-21 | Process for the preparation of acid amides, use of the process and morpholino-ethyl isocyanide |
Country Status (5)
Country | Link |
---|---|
US (1) | US4442029A (en, 2012) |
EP (1) | EP0029909B1 (en, 2012) |
JP (1) | JPS5665851A (en, 2012) |
AT (1) | ATE8499T1 (en, 2012) |
DE (2) | DE2942606A1 (en, 2012) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH02191285A (ja) * | 1988-06-28 | 1990-07-27 | Ajinomoto Co Inc | アミド化合物の製造方法 |
WO1993002697A1 (en) * | 1991-08-08 | 1993-02-18 | Amylin Pharmaceuticals, Inc. | Production of peptide amides |
EP0983290B1 (de) * | 1997-05-14 | 2004-03-03 | Morphochem AG | Verfahren zur herstellung von polymeren, die nucleobasen als seitengruppen aufweisen |
CA2247580A1 (en) | 1997-10-03 | 1999-04-03 | F. Hoffmann-La Roche Ag | Process for preparing chiral succinic acid derivatives |
US6316633B1 (en) | 1998-09-15 | 2001-11-13 | Hoffman-La Roche Inc. | Process for manufacture of chiral succinic acid derivatives |
EP2409983A1 (en) | 2010-07-19 | 2012-01-25 | Leibniz-Institut für Pflanzenbiochemie (IPB) | Tubulysin analogues |
PL2570468T3 (pl) | 2011-09-13 | 2014-04-30 | Bundesdruckerei Gmbh | Luminofor antystokesowski jako znacznik zabezpieczający w zabezpieczanych dokumentach |
WO2013135511A1 (en) | 2012-03-12 | 2013-09-19 | Imax Discovery Gmbh | N-(2,4-dimethylpentan-3-yl)-methylbenzamides and their use as flavoring agents |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3933783A (en) * | 1971-12-27 | 1976-01-20 | Ajinomoto Co., Inc. | Formation of peptide bonds in the presence of isonitriles |
JPS5133521B2 (en, 2012) * | 1972-11-17 | 1976-09-20 |
-
1979
- 1979-10-22 DE DE19792942606 patent/DE2942606A1/de not_active Withdrawn
-
1980
- 1980-10-21 EP EP80106416A patent/EP0029909B1/de not_active Expired
- 1980-10-21 AT AT80106416T patent/ATE8499T1/de not_active IP Right Cessation
- 1980-10-21 DE DE8080106416T patent/DE3068616D1/de not_active Expired
- 1980-10-22 JP JP14699280A patent/JPS5665851A/ja active Granted
-
1983
- 1983-01-25 US US06/460,881 patent/US4442029A/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
JPH0346460B2 (en, 2012) | 1991-07-16 |
ATE8499T1 (de) | 1984-08-15 |
EP0029909A1 (de) | 1981-06-10 |
US4442029A (en) | 1984-04-10 |
JPS5665851A (en) | 1981-06-03 |
DE3068616D1 (en) | 1984-08-23 |
EP0029909B1 (de) | 1984-07-18 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
8139 | Disposal/non-payment of the annual fee |