ES316093A1 - Procedure for the manufacture of l - (-) -alfa methyl - beta- (3, 4-dihydroxypenyl) -alanin. (Machine-translation by Google Translate, not legally binding) - Google Patents
Procedure for the manufacture of l - (-) -alfa methyl - beta- (3, 4-dihydroxypenyl) -alanin. (Machine-translation by Google Translate, not legally binding)Info
- Publication number
- ES316093A1 ES316093A1 ES0316093A ES316093A ES316093A1 ES 316093 A1 ES316093 A1 ES 316093A1 ES 0316093 A ES0316093 A ES 0316093A ES 316093 A ES316093 A ES 316093A ES 316093 A1 ES316093 A1 ES 316093A1
- Authority
- ES
- Spain
- Prior art keywords
- benzylaminonitrile
- hydrolysis
- alpha
- methyl
- sulphonic acid
- 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
L - ( - ) - [alpha] - Methyl - # - (3,4 - dihydroxyphenyl)-alanine is prepared by reacting 3,4- dimethoxyphenylacetone, or the bisulphite adduct thereof with an alkali metal cyanide and benzylamine, the [alpha]-benzylamino-[alpha]-(3,4-dimethoxybenzyl)-propionitrile obtained being resolved by using mol. d-(+)-camphor-sulphonic acid per mol. of racemate, the resolution being carried out in aqueous suspension in the presence of an organic solvent which is immiscible with water and with ice-cooling or at a temperature of 10-15 C., the precipitated camphor-sulphonic acid salt of the L-(+)- benzylaminonitrile being separated and converted into the free L-(+)-benzylaminonitrile, this conversion being carried out with cooling in an aqueous suspension in the presence of a waterimmiscible solvent, and the D-isomer remaining in the mother liquor being racemized in an alkaline medium to give the D,L-benzylaminonitrile which can be returned to the resolution step, the L (+) - [alpha] - benzylamino - [alpha] - (3,4 - dimethoxybenzyl) - propionitrile obtained then being converted into L-( - )-[alpha]-methyl-#-(3,4- dihydroxyphenyl)-alanine by first partially hydrolysing it with concentrated sulphuric acid to give an amide of formula followed, in any order, by debenzylation by catalytic hydrogenation, demethylation by hydrolysis, removal of the sulphonic acid group by hydrolysis and conversion of the amide group into a free carboxylic acid group by hydrolysis.L - (-) - a - Methyl - b - (3,4 - dihydroxyphenyl)-alanine is prepared by reacting 3,4-dimethoxyphenylacetone, or the bisulphite adduct thereof with an alkali metal cyanide and benzylamine, the a-benzylamino-a-(3,4-dimethoxybenzyl) -propionitrile obtained being resolved by using 1/2 mol. d-(+)-camphor-sulphonic acid per mol. of racemate, the resolution being carried out in aqueous suspension in the presence of an organic solvent which is immiscible with water and with ice-cooling or at a temperature of 10-15 DEG C., the precipitated camphor-sulphonic acid salt of the L-(+)-benzylaminonitrile being separated and converted into the free L-(+)-benzylaminonitrile, this conversion being carried out with cooling in an aqueous suspension in the presence of a water-immiscible solvent, and the D-isomer remaining in the mother liquor being racemized in an alkaline medium to give the D,L-benzylaminonitrile which can be returned to the resolution step, the L - (+) - a - benzylamino - a - (3,4 - dimethoxybenzyl) - propionitrile obtained then being converted into L-(-)-a-methyl-b-(3,4 -dihydroxyphenyl)-alanine by first partially hydrolysing it with concentrated sulphuric acid to give an amide of formula <FORM:1050838/C2/1> followed, in any order, by debenzylation by catalytic hydrogenation, demethylation by hydrolysis, removal of the sulphonic acid group by hydrolysis and conversion of the amide group into a free carboxylic acid group by hydrolysis.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEB78032A DE1235946B (en) | 1964-08-08 | 1964-08-08 | Process for the preparation of L- (í¬) -alpha-methyl-beta- (3, 4-dihydroxyphenyl) -alanine |
Publications (1)
Publication Number | Publication Date |
---|---|
ES316093A1 true ES316093A1 (en) | 1965-12-01 |
Family
ID=6979712
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES0316093A Expired ES316093A1 (en) | 1964-08-08 | 1965-08-03 | Procedure for the manufacture of l - (-) -alfa methyl - beta- (3, 4-dihydroxypenyl) -alanin. (Machine-translation by Google Translate, not legally binding) |
Country Status (12)
Country | Link |
---|---|
AT (1) | AT257581B (en) |
BE (1) | BE668028A (en) |
CH (1) | CH476686A (en) |
DE (1) | DE1235946B (en) |
DK (1) | DK111621B (en) |
ES (1) | ES316093A1 (en) |
FI (1) | FI44005C (en) |
FR (1) | FR1462253A (en) |
GB (1) | GB1050838A (en) |
IL (1) | IL24094A (en) |
LU (1) | LU49278A1 (en) |
NL (1) | NL6510306A (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102633692B (en) * | 2012-04-11 | 2014-04-09 | 上海康福赛尔医药科技有限公司 | Method for preparing optically active L-D-3-bromocamphor-8-sulfonic acid |
-
0
- GB GB1050838D patent/GB1050838A/en active Active
-
1964
- 1964-08-08 DE DEB78032A patent/DE1235946B/en active Pending
-
1965
- 1965-08-03 ES ES0316093A patent/ES316093A1/en not_active Expired
- 1965-08-05 FR FR27355A patent/FR1462253A/en not_active Expired
- 1965-08-05 DK DK402265A patent/DK111621B/en unknown
- 1965-08-05 CH CH1099265A patent/CH476686A/en not_active IP Right Cessation
- 1965-08-05 IL IL2409465A patent/IL24094A/en unknown
- 1965-08-06 AT AT728465A patent/AT257581B/en active
- 1965-08-06 BE BE668028D patent/BE668028A/xx unknown
- 1965-08-06 NL NL6510306A patent/NL6510306A/xx unknown
- 1965-08-06 FI FI190265A patent/FI44005C/en active
- 1965-08-06 LU LU49278A patent/LU49278A1/xx unknown
Also Published As
Publication number | Publication date |
---|---|
DK111621B (en) | 1968-09-23 |
FR1462253A (en) | 1966-04-15 |
GB1050838A (en) | |
BE668028A (en) | 1966-02-07 |
NL6510306A (en) | 1966-02-09 |
FI44005C (en) | 1971-08-10 |
DE1235946B (en) | 1967-03-09 |
FI44005B (en) | 1971-04-30 |
IL24094A (en) | 1969-02-27 |
LU49278A1 (en) | 1965-10-06 |
CH476686A (en) | 1969-08-15 |
AT257581B (en) | 1967-10-10 |
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