GB812541A - Process for the production of n,n-dibenzylamino acids - Google Patents
Process for the production of n,n-dibenzylamino acidsInfo
- Publication number
- GB812541A GB812541A GB19874/55A GB1987455A GB812541A GB 812541 A GB812541 A GB 812541A GB 19874/55 A GB19874/55 A GB 19874/55A GB 1987455 A GB1987455 A GB 1987455A GB 812541 A GB812541 A GB 812541A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dibenzyl
- acid
- diol
- similarly
- give
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises nitriles of the formula: <FORM:0812541/IV (b)/1> (wherein R is hydrogen or an alkyl radical and n is zero or 1 to 8, except that when R is hydrogen n is not zero) and their preparation by condensing at an elevated temperature dibenzylamine with the appropriate a -hydroxynitrile. This process may be combined with subsequent hydrolysis of the nitrile with a strong acid to give first the corresponding amide and then the corresponding N:N-dibenzylamino acid. The condensation is preferably effected in ethanol, and the hydrolysis of the nitrile is preferably effected with concentrated sulphuric acid and that of the amide with aqueous hydrochloric acid, advantageously containing acetic acid. The above processes may also be combined with resolution of the N:N-dibenzylamino acids by reacting L-(+)- or D-(-)-threo-1-p-nitrophenyl-2-aminopropane-1:3-diol with a mixture in any proportions of the enantiomorphs of the acid in an aqueous aliphatic alcohol containing at most 6 carbon atoms, separating the resulting sparingly soluble salt of one of the said enantiomorphs with the optically active diol and liberating the enantiomorph therefrom. In examples: (1) lactonitrile and dibenzylamine give N:N - dibenzyl - a - aminopropionitrile, this is hydrolysed with sulphuric acid to N:N-dibenzyl - a - aminopropionamide and this is hydrolysed with hydrochloric acid to N:N-dibenzyl - DL - a - alanine hydrochloride, from which the free base is liberated; (2) N:N - dibenzyl - a - aminobutyronitrile, the corresponding amide and N:N-dibenzyl-DL-a -aminobutyric acid are similarly prepared; (3) N:N - dibenzyl - a - aminovaleronitrile and the corresponding amide are prepared as in (1) and the latter is hydrolysed with a hydrochloric/acetic acid mixture to N:N-dibenzyl-DL - norvaline; (4) N:N - dibenzyl - a - aminoisovaleronitrile, the corresponding amide and N:N - dibenzyl - DL - valine are similarly prepared; (5) N:N-dibenzyl-a -aminoisocapronitrile, the corresponding amide and N:N-dibenzyl - DL - leucine are similarly prepared; (6) DL-N:N-dibenzylalanine and L - (+) - threo - 1 - p - nitrophenyl - 2 - aminopropane - 1:3 - diol (hereinafter called the L-diol) are refluxed in aqueous alcohol to give, on crystallization, the salt of the L-diol with the L - (-) - N:N - dibenzylalanine; the L-diol is recovered from the mother liquors by addition of sodium hydroxide and after removal of this the filtrate is worked up to give D - (+) - N:N - dibenzylalanine which is immediately converted to a salt with D-(-)-threo - 1 - p - nitrophenyl - 2 - aminopropane-1:3-diol; from the salt of the L-diol with L - (-) - N:N - dibenzylalanine the free amino acid is liberated and this is then hydrogenolysed in presence of a carbon palladium catalyst to give L-(+)-alanine hydrochloride; (7) DL - N:N - dibenzylvaline is similarly resolved and the L-(-)-isomer similarly hydrogenolized to L-(+)-valine; (8) DL-N:N-dibenzylnorvaline is similarly resolved and the L - (-) - isomer hydrogenolysed to L - (+)-norvaline; (9) DL-N:N-a -dibenzyl-aminobutyric acid is resolved similarly and the L - (-) - siomer hydrogenolysed to L - (+) - a - aminobutyric acid; (10) DL-N:N-dibenzylleucine is resolved similarly and the L-(-)-isomer hydrogenolysed to L-(-)-leucine. Specifications 423,735, 512,691, [both in Group IV], 770,575 and 812,543 are referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR812541X | 1954-08-03 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB812541A true GB812541A (en) | 1959-04-29 |
Family
ID=9265672
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB19874/55A Expired GB812541A (en) | 1954-08-03 | 1955-07-08 | Process for the production of n,n-dibenzylamino acids |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB812541A (en) |
-
1955
- 1955-07-08 GB GB19874/55A patent/GB812541A/en not_active Expired
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