FR2531078A1 - Prodece de synthese d'alpha alkylamino aldehydes - Google Patents
Prodece de synthese d'alpha alkylamino aldehydes Download PDFInfo
- Publication number
- FR2531078A1 FR2531078A1 FR8213385A FR8213385A FR2531078A1 FR 2531078 A1 FR2531078 A1 FR 2531078A1 FR 8213385 A FR8213385 A FR 8213385A FR 8213385 A FR8213385 A FR 8213385A FR 2531078 A1 FR2531078 A1 FR 2531078A1
- Authority
- FR
- France
- Prior art keywords
- ppm
- aldehydes
- alpha
- alkylamino
- synthesis product
- 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
Links
- 230000015572 biosynthetic process Effects 0.000 title description 6
- 238000003786 synthesis reaction Methods 0.000 title description 6
- 150000001299 aldehydes Chemical class 0.000 title 1
- -1 alkyl amino aldehydes Chemical class 0.000 abstract description 13
- 238000000034 method Methods 0.000 abstract description 8
- 125000000217 alkyl group Chemical group 0.000 abstract description 5
- 150000001413 amino acids Chemical class 0.000 abstract description 5
- 238000002360 preparation method Methods 0.000 abstract description 5
- 150000004678 hydrides Chemical class 0.000 abstract description 4
- 125000003710 aryl alkyl group Chemical group 0.000 abstract description 3
- KRKPYFLIYNGWTE-UHFFFAOYSA-N n,o-dimethylhydroxylamine Chemical compound CNOC KRKPYFLIYNGWTE-UHFFFAOYSA-N 0.000 abstract description 3
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 abstract description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 4
- 239000012047 saturated solution Substances 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 150000003573 thiols Chemical group 0.000 description 2
- OMFSJRHPFYVJSP-UHFFFAOYSA-N 2,3,4,5-tetramethylfuran Chemical compound CC=1OC(C)=C(C)C=1C OMFSJRHPFYVJSP-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 101000913968 Ipomoea purpurea Chalcone synthase C Proteins 0.000 description 1
- 150000008575 L-amino acids Chemical class 0.000 description 1
- 229920006063 Lamide® Polymers 0.000 description 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
- MDXGYYOJGPFFJL-QMMMGPOBSA-N N(alpha)-t-butoxycarbonyl-L-leucine Chemical compound CC(C)C[C@@H](C(O)=O)NC(=O)OC(C)(C)C MDXGYYOJGPFFJL-QMMMGPOBSA-N 0.000 description 1
- 101000907988 Petunia hybrida Chalcone-flavanone isomerase C Proteins 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- USZLCYNVCCDPLQ-UHFFFAOYSA-N hydron;n-methoxymethanamine;chloride Chemical compound Cl.CNOC USZLCYNVCCDPLQ-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 125000001909 leucine group Chemical group [H]N(*)C(C(*)=O)C([H])([H])C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- XCVNDBIXFPGMIW-UHFFFAOYSA-N n-ethylpropan-1-amine Chemical compound CCCNCC XCVNDBIXFPGMIW-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 239000012070 reactive reagent Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C223/00—Compounds containing amino and —CHO groups bound to the same carbon skeleton
- C07C223/02—Compounds containing amino and —CHO groups bound to the same carbon skeleton having amino groups bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8213385A FR2531078A1 (fr) | 1982-07-30 | 1982-07-30 | Prodece de synthese d'alpha alkylamino aldehydes |
| AT83401519T ATE16381T1 (de) | 1982-07-30 | 1983-07-25 | Verfahren zur herstellung von alpha-alkylaminoaldehyden. |
| DE8383401519T DE3361174D1 (en) | 1982-07-30 | 1983-07-25 | Process for the preparation of alphaalkylaminoaldehydes |
| EP83401519A EP0100717B1 (fr) | 1982-07-30 | 1983-07-25 | Procédé de synthèse d'alphaalkyl amino aldéhydes |
| JP58139325A JPS5984850A (ja) | 1982-07-30 | 1983-07-29 | α−アルキルアミノアルデヒドの合成方法 |
| CA000433574A CA1200556A (en) | 1982-07-30 | 1983-07-29 | Process for synthesis of alpha alkyl amino aldehydes |
| US06/760,524 US4886914A (en) | 1982-07-30 | 1985-07-30 | Process for synthesis of alpha aklyl amino aldehydes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8213385A FR2531078A1 (fr) | 1982-07-30 | 1982-07-30 | Prodece de synthese d'alpha alkylamino aldehydes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2531078A1 true FR2531078A1 (fr) | 1984-02-03 |
| FR2531078B1 FR2531078B1 (enExample) | 1985-01-11 |
Family
ID=9276510
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8213385A Granted FR2531078A1 (fr) | 1982-07-30 | 1982-07-30 | Prodece de synthese d'alpha alkylamino aldehydes |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4886914A (enExample) |
| EP (1) | EP0100717B1 (enExample) |
| JP (1) | JPS5984850A (enExample) |
| AT (1) | ATE16381T1 (enExample) |
| CA (1) | CA1200556A (enExample) |
| DE (1) | DE3361174D1 (enExample) |
| FR (1) | FR2531078A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3711911A1 (de) * | 1987-04-08 | 1988-10-20 | Bayer Ag | Optisch aktive (alpha)-aminoaldehyde, verfahren zu ihrer herstellung und ihre verwendung zur stereoselektiven herstellung optisch aktiver ss-aminoalkohole |
| US5198586A (en) * | 1987-08-12 | 1993-03-30 | Sanofi | Process for the preparation of phenylethanolaminotetralins |
| US5399763A (en) * | 1993-02-01 | 1995-03-21 | Nippon Kayaku Kabushiki Kaisha | Process for preparing optically active 2-aminopropanal |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3027407A (en) * | 1960-05-26 | 1962-03-27 | Cobb Chemical Lab | Phenoxyacetamides |
| US3166589A (en) * | 1962-11-20 | 1965-01-19 | Velsicol Chemical Corp | Phenoxyacetamides for the control of pests |
| US3280226A (en) * | 1964-02-05 | 1966-10-18 | Velsicol Chemical Corp | Bis-(carbamyl) alkyl amides of phorphorus acid esters |
| US3726881A (en) * | 1970-12-28 | 1973-04-10 | Richter Gedeon Vegyeszet | N-aminoxy-acetyl-n'-isonicotinoyl-hydrazine and the pharmaceutically acceptable salts thereof |
-
1982
- 1982-07-30 FR FR8213385A patent/FR2531078A1/fr active Granted
-
1983
- 1983-07-25 DE DE8383401519T patent/DE3361174D1/de not_active Expired
- 1983-07-25 EP EP83401519A patent/EP0100717B1/fr not_active Expired
- 1983-07-25 AT AT83401519T patent/ATE16381T1/de active
- 1983-07-29 CA CA000433574A patent/CA1200556A/en not_active Expired
- 1983-07-29 JP JP58139325A patent/JPS5984850A/ja active Pending
-
1985
- 1985-07-30 US US06/760,524 patent/US4886914A/en not_active Expired - Fee Related
Non-Patent Citations (2)
| Title |
|---|
| J. ORG. CHEM., volume 46, no. 23, 1981, AMERICAN CHEMICAL SOC. (WASHINGTON D.C., US) C. FREEMAN STANFIELD et al. "Preparation of protected amino aldehydes", pages 4797-4798 * |
| SAUL PATAI: THE CHEMISTRY OF FUNCTIONAL GROUPS. THE CHEMISTRY OF THE CARBONYL GROUP", 1966, Interscience Publishers, London, New York, Sydney, Toronto R.C. FUSON "Formation from carboxylic acids and their derivatives", pages 221-225 * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0100717A1 (fr) | 1984-02-15 |
| ATE16381T1 (de) | 1985-11-15 |
| FR2531078B1 (enExample) | 1985-01-11 |
| CA1200556A (en) | 1986-02-11 |
| EP0100717B1 (fr) | 1985-11-06 |
| DE3361174D1 (en) | 1985-12-12 |
| US4886914A (en) | 1989-12-12 |
| JPS5984850A (ja) | 1984-05-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |