GB814063A - Process for the preparation of ª‰-hydroxy-ª‡-amino acids - Google Patents
Process for the preparation of ª‰-hydroxy-ª‡-amino acidsInfo
- Publication number
- GB814063A GB814063A GB3928357A GB3928357A GB814063A GB 814063 A GB814063 A GB 814063A GB 3928357 A GB3928357 A GB 3928357A GB 3928357 A GB3928357 A GB 3928357A GB 814063 A GB814063 A GB 814063A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxy
- glycine
- preparation
- metal complex
- complex salt
- 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
- 238000002360 preparation method Methods 0.000 title abstract 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-N glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 abstract 5
- 239000011780 sodium chloride Substances 0.000 abstract 4
- 239000004471 Glycine Substances 0.000 abstract 3
- 239000003054 catalyst Substances 0.000 abstract 3
- -1 metal complex salt Chemical class 0.000 abstract 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- CXIYBDIJKQJUMN-UHFFFAOYSA-N 2-anilino-3-hydroxypropanoic acid Chemical compound OCC(C(O)=O)NC1=CC=CC=C1 CXIYBDIJKQJUMN-UHFFFAOYSA-N 0.000 abstract 1
- MTCFGRXMJLQNBG-UWTATZPHSA-N D-serine Chemical compound OC[C@@H](N)C(O)=O MTCFGRXMJLQNBG-UWTATZPHSA-N 0.000 abstract 1
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 abstract 1
- 239000004473 Threonine Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000001413 amino acids Chemical class 0.000 abstract 1
- 239000003957 anion exchange resin Substances 0.000 abstract 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract 1
- 239000011575 calcium Substances 0.000 abstract 1
- 229910052791 calcium Inorganic materials 0.000 abstract 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 230000000875 corresponding Effects 0.000 abstract 1
- 150000001913 cyanates Chemical class 0.000 abstract 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 abstract 1
- 239000003456 ion exchange resin Substances 0.000 abstract 1
- 229920003303 ion-exchange polymer Polymers 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 1
- 235000011118 potassium hydroxide Nutrition 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/16—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions not involving the amino or carboxyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
b -Hydroxy-a -amino acids of the formula R.CH(OH).CH(NH2)COOH, wherein R is an hydrogen atom or an alkyl or aryl radical, are prepared by condensing a metal complex salt of glycine with an aldehyde of the formula R.CHO in the presence of a catalyst consisting of an inorganic and/or an organic base to produce a corresponding metal complex salt of a b -hydroxy-a -amino acid, removing the metal by treatment with hydrogen sulphide or an ion exchange resin and recovering the free amino-acid. Suitable starting materials are the copper, zinc or calcium complex salts of glycine (the preparation of the former two being described). Condensation temperatures are preferably between 30 DEG and 80 DEG C. Exemplified catalysts are sodium and potassium hydroxides, carbonates and cyanates, amines (e.g. pyridine) and anion exchange resins. Between 0.1 and 0.2 mol. of catalyst may be used per mol. of glycine metal complex salt. The examples describe the preparation of threonine, serine and phenylserine.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB814063A true GB814063A (en) | 1959-05-27 |
Family
ID=1745515
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3928357A Expired GB814063A (en) | 1957-12-17 | Process for the preparation of ª‰-hydroxy-ª‡-amino acids |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB814063A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003049850A2 (en) * | 2001-12-11 | 2003-06-19 | Pancosma Societe Anonyme Pour L'industrie Des Produits Biochimiques | Powder trace element, method and device for making same |
| FR2843752A1 (en) * | 2002-08-26 | 2004-02-27 | Pancosma Sa Pour L Ind Des Pro | New stable, crystalline organometallic complexes of glycine with metals, e.g. cobalt, magnesium, iron, zinc, manganese or copper, useful as bioavailable metal sources for humans or animals |
-
1957
- 1957-12-17 GB GB3928357A patent/GB814063A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003049850A2 (en) * | 2001-12-11 | 2003-06-19 | Pancosma Societe Anonyme Pour L'industrie Des Produits Biochimiques | Powder trace element, method and device for making same |
| WO2003049850A3 (en) * | 2001-12-11 | 2003-10-23 | Pancosma Sa Pour L Ind Des Pro | Powder trace element, method and device for making same |
| FR2843752A1 (en) * | 2002-08-26 | 2004-02-27 | Pancosma Sa Pour L Ind Des Pro | New stable, crystalline organometallic complexes of glycine with metals, e.g. cobalt, magnesium, iron, zinc, manganese or copper, useful as bioavailable metal sources for humans or animals |
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