GB832003A - Steric inversion of allothreonine and intermediates of inversion - Google Patents
Steric inversion of allothreonine and intermediates of inversionInfo
- Publication number
- GB832003A GB832003A GB17733/57A GB1773357A GB832003A GB 832003 A GB832003 A GB 832003A GB 17733/57 A GB17733/57 A GB 17733/57A GB 1773357 A GB1773357 A GB 1773357A GB 832003 A GB832003 A GB 832003A
- Authority
- GB
- United Kingdom
- Prior art keywords
- threonine
- give
- product
- acid
- oxazoline
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
2 - Aryl - 5 - methyl - D 2 - oxazoline - 4 - carboxylic acids and/or a -aroylamino-b -hydroxybutyric acids are prepared by condensing allothreonine, which may be admixed with threonine, with an aryl nitrile in the presence of an alkaline condensing agent. This agent is conveniently an alkali metal alcoholate, the reaction advantageously being effected in a lower aliphatic alcohol. The nature of the product is stated probably to depend on the length of time that the reaction mixture is allowed to stand and on the other reaction conditions. The invention also comprises the additional step of hydrolysing either product or a mixture thereof with an acid hydrolysing agent to give threonine. In examples: (1) DL-allothreonine containing a small amount of DL-threonine is left to stand for several days with sodium methoxide and benzonitrile, the reaction mixture is diluted with water, unreacted benzonitrile is removed by shaking with benzene, and the aqueous solution is passed through a slightly acid ion-exchanger and then concentrated to give 2-phenyl-5-methyl- D 2-oxazoline - 4 - carboxylic acid; (2) 2 - p - tolyl - 5 - methyl - D 2 - oxazoline - 4 - carboxylic acid is similarly prepared; (3) the reaction mixture of Example (1) is allowed to stand for 9 days, the solvent is distilled off and the residue is left standing for 7 more days before working up as in Example (1) to give DL-N-benzoylthreonine; (4) the product of (1) is heated with dilute hydrochloric acid to give, on working up, DL-threonine; and (5) the product of (3) is heated with dilute sulphuric acid to give, on working up, DL-threonine.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP832003X | 1956-06-05 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB832003A true GB832003A (en) | 1960-04-06 |
Family
ID=13795665
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB17733/57A Expired GB832003A (en) | 1956-06-05 | 1957-06-04 | Steric inversion of allothreonine and intermediates of inversion |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB832003A (en) |
-
1957
- 1957-06-04 GB GB17733/57A patent/GB832003A/en not_active Expired
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