IT1306737B1 - Preparation of L-carnitine inner salt in high yields by reducing succinic acid derivative and treating with base and then trimethylamine - Google Patents
Preparation of L-carnitine inner salt in high yields by reducing succinic acid derivative and treating with base and then trimethylamineInfo
- Publication number
- IT1306737B1 IT1306737B1 ITRM990670A IT1306737B1 IT 1306737 B1 IT1306737 B1 IT 1306737B1 IT RM990670 A ITRM990670 A IT RM990670A IT 1306737 B1 IT1306737 B1 IT 1306737B1
- Authority
- IT
- Italy
- Prior art keywords
- preparation
- trimethylamine
- treating
- succinic acid
- base
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title abstract 6
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 title abstract 6
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 title abstract 3
- 150000003443 succinic acid derivatives Chemical class 0.000 title abstract 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract 6
- 238000000034 method Methods 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- 239000011780 sodium chloride Substances 0.000 abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 abstract 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 abstract 2
- QEGKXSHUKXMDRW-REOHCLBHSA-N (2s)-2-chlorobutanedioic acid Chemical compound OC(=O)C[C@H](Cl)C(O)=O QEGKXSHUKXMDRW-REOHCLBHSA-N 0.000 abstract 1
- ZKASOSSCYHQHDU-REOHCLBHSA-N (2s)-2-chlorobutanedioyl dichloride Chemical compound ClC(=O)[C@@H](Cl)CC(Cl)=O ZKASOSSCYHQHDU-REOHCLBHSA-N 0.000 abstract 1
- YWWMSXSIVPRWJY-VKHMYHEASA-N (2s)-2-methylsulfonyloxybutanedioic acid Chemical compound CS(=O)(=O)O[C@H](C(O)=O)CC(O)=O YWWMSXSIVPRWJY-VKHMYHEASA-N 0.000 abstract 1
- MCMLJMMLKJFXBH-VKHMYHEASA-N (3s)-3-chloro-4-methoxy-4-oxobutanoic acid Chemical compound COC(=O)[C@@H](Cl)CC(O)=O MCMLJMMLKJFXBH-VKHMYHEASA-N 0.000 abstract 1
- RIHWJROUZAYQGA-REOHCLBHSA-N (3s)-3-chlorooxolane-2,5-dione Chemical compound Cl[C@H]1CC(=O)OC1=O RIHWJROUZAYQGA-REOHCLBHSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 125000005905 mesyloxy group Chemical group 0.000 abstract 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
- 238000001556 precipitation Methods 0.000 abstract 1
- 235000010288 sodium nitrite Nutrition 0.000 abstract 1
- 239000001384 succinic acid Substances 0.000 abstract 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 abstract 1
- 239000003643 water by type Substances 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Preparation of L-carnitine inner salt comprises: (a) reducing a succinic acid derivative (I); and (b) treating with a base and then with trimethylamine. Preparation of L-carnitine inner salt comprises: (a) reducing a succinic acid derivative of formula (I); and (b) treating with a base and then with trimethylamine. [Image] X 1, X 2OH, 1-4C alkoxy, phenoxy or halo; or X 1+X 2O; Y : halo, mesyloxy or tosyloxy. Independent claims are also included for: (i) 1-methyl hydrogen (S)-2-chlorosuccinate, (S)-2-chlorosuccinoyldichloride and (S)-methanesulfonyloxysuccinic acid as intermediates in the above process; (ii) a process for the preparation of (S)-(-)-chlorosuccinic acid comprising reacting (S)(+)-aspartic acid and sodium nitrite in a hydrochloric acid-aqueous milieu in the presence of sodium chloride in a (S)-(+)-aspartic acid:sodium chloride ratio of 1:0.3-1:0.5, the improvement consisting of: (a) the isolation of the product by precipitation with cooling; (b) using the mother waters from a previous preparation (a) as at least partial substitutes for the sodium chloride and hydrochloric acid; and (iii) a process for the preparation of (S)-chlorosuccinic anhydride comprising reacting (S)-(-)-succinic acid prepared by a process (ii) and acetic anhydride.
Priority Applications (26)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1999RM000670 IT1306737B1 (en) | 1999-10-29 | 1999-10-29 | Preparation of L-carnitine inner salt in high yields by reducing succinic acid derivative and treating with base and then trimethylamine |
| CZ20013816A CZ20013816A3 (en) | 1999-05-18 | 2000-05-12 | Process for preparing R-(-)-carnitine from S-(-)-chlorosuccinic acid or derivatives thereof |
| PL351646A PL203993B1 (en) | 1999-05-18 | 2000-05-12 | Process for preparing r-(-)-carnitine from s-(-)-chlorosuccinic acid or from a derivative thereof |
| CNB008076502A CN1158244C (en) | 1999-05-18 | 2000-05-12 | Method for preparing R-(one)-carnitine from S-(one)-chlorosuccinic acid or its derivatives |
| EP00927737A EP1187805B1 (en) | 1999-05-18 | 2000-05-12 | Process for preparing r-(-)-carnitine from s-(-)-chlorosuccinic acid or from a derivative thereof |
| SK1601-2001A SK286155B6 (en) | 1999-05-18 | 2000-05-12 | Process for the preparation of L-carnitine inner salt, intermediates and their use |
| PCT/IT2000/000187 WO2000069808A1 (en) | 1999-05-18 | 2000-05-12 | Process for preparing r-(-)-carnitine from s-(-)-chlorosuccinic acid or from a derivative thereof |
| PT00927737T PT1187805E (en) | 1999-05-18 | 2000-05-12 | Process for preparing r-(-)-carnitine from s-(-)-chlorosuccinic acid or from a derivative thereof |
| KR1020017014397A KR100684379B1 (en) | 1999-05-18 | 2000-05-12 | Process for preparing R-(-)-carnitine from S-(-)-chlorosuccinic acid or derivatives thereof |
| US09/959,717 US6677476B1 (en) | 1999-05-18 | 2000-05-12 | Process for preparing R-(-) -carnitine from S-(-)-chlorosuccinic acid or from a derivative thereof |
| HU0201418A HUP0201418A3 (en) | 1999-05-18 | 2000-05-12 | Process for preparing r-(-)-carnitine from s-(-)-chlorosuccinic acid or from a derative thereof |
| DE60032139T DE60032139T2 (en) | 1999-05-18 | 2000-05-12 | METHOD FOR THE PRODUCTION OF R - (-) CARNITINE FROM S - (-) - CHLOROBINIC ACID OR FROM ITS DERIVATIVES |
| SI200030921T SI1187805T1 (en) | 1999-05-18 | 2000-05-12 | Process for preparing r-(-)-carnitine from s-(-)-chlorosuccinic acid or from a derivative thereof |
| ES00927737T ES2277838T3 (en) | 1999-05-18 | 2000-05-12 | PROCESS TO PREPARE R - (-) - CARNITINE FROM ACID S - (-) - CHLOROSUCCINIC OR FROM A DERIVATIVE OF THE SAME. |
| AU46121/00A AU4612100A (en) | 1999-05-18 | 2000-05-12 | Process for preparing r-(-)-carnitine from s-(-)-chlorosuccinic acid or from a derivative thereof |
| DK00927737T DK1187805T3 (en) | 1999-05-18 | 2000-05-12 | Process for the preparation of R - (-) - carnitine from S - (-) - chloro succinic acid or from a derivative thereof |
| KR1020067021556A KR100789468B1 (en) | 1999-05-18 | 2000-05-12 | Method for producing S-(-)-chlorosuccinic acid |
| EP04013530A EP1468979A1 (en) | 1999-05-18 | 2000-05-12 | Process for preparing S-(-)-chlorosuccinic acid |
| CA002372424A CA2372424A1 (en) | 1999-05-18 | 2000-05-12 | Process for preparing r-(-)-carnitine from s-(-)-chlorosuccinic acid or from a derivative thereof |
| MXPA01011758A MXPA01011758A (en) | 1999-05-18 | 2000-05-12 | Process for preparing r-(-)-carnitine from s-(-)-chlorosuccinic acid or from a derivative thereof. |
| AT00927737T ATE346838T1 (en) | 1999-05-18 | 2000-05-12 | METHOD FOR PRODUCING R-(-)-CARNITINE FROM S-(-)-CHLOROSUNCRIC ACID OR FROM ONE DERIVATIVES THEREOF |
| JP2000618226A JP4584464B2 (en) | 1999-05-18 | 2000-05-12 | Process for preparing R-(-)-carnitine from S-(-)-chlorosuccinic acid or its derivatives |
| US10/716,453 US6984739B2 (en) | 1999-05-18 | 2003-11-20 | Process for preparing R-(−)-carnitin from S-(−)-chlorosuccinic acid or from a derivative thereof |
| US11/175,356 US7247747B2 (en) | 1999-05-18 | 2005-07-07 | Process for preparing R-(-)carnitine from S-(-)-chlorosuccinic acid or from a derivative thereof |
| CY20071100268T CY1107566T1 (en) | 1999-05-18 | 2007-02-26 | METHOD FOR THE PRODUCTION OF R - (-) - CARNITINE FROM S - (-) CHLOROIDIC ACID OR FROM A PRODUCER |
| JP2010153891A JP2010229157A (en) | 1999-05-18 | 2010-07-06 | Method for preparing r-(-)-carnitine from s-(-)-chlorosuccinic acid or derivative thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1999RM000670 IT1306737B1 (en) | 1999-10-29 | 1999-10-29 | Preparation of L-carnitine inner salt in high yields by reducing succinic acid derivative and treating with base and then trimethylamine |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| ITRM990670A0 ITRM990670A0 (en) | 1999-10-29 |
| ITRM990670A1 ITRM990670A1 (en) | 2001-04-29 |
| IT1306737B1 true IT1306737B1 (en) | 2001-10-02 |
Family
ID=11407030
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IT1999RM000670 IT1306737B1 (en) | 1999-05-18 | 1999-10-29 | Preparation of L-carnitine inner salt in high yields by reducing succinic acid derivative and treating with base and then trimethylamine |
Country Status (1)
| Country | Link |
|---|---|
| IT (1) | IT1306737B1 (en) |
-
1999
- 1999-10-29 IT IT1999RM000670 patent/IT1306737B1/en active
Also Published As
| Publication number | Publication date |
|---|---|
| ITRM990670A0 (en) | 1999-10-29 |
| ITRM990670A1 (en) | 2001-04-29 |
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