GB600893A - Manufacture of acylated aliphatic amino carboxylic acid amides - Google Patents
Manufacture of acylated aliphatic amino carboxylic acid amidesInfo
- Publication number
- GB600893A GB600893A GB3303645A GB3303645A GB600893A GB 600893 A GB600893 A GB 600893A GB 3303645 A GB3303645 A GB 3303645A GB 3303645 A GB3303645 A GB 3303645A GB 600893 A GB600893 A GB 600893A
- Authority
- GB
- United Kingdom
- Prior art keywords
- crotonyl
- butyric acid
- acylated
- chloride
- reacted
- 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
- -1 acylated aliphatic amino carboxylic acid amides Chemical class 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 abstract 5
- RJUIDDKTATZJFE-NSCUHMNNSA-N (E)-but-2-enoyl chloride Chemical compound C\C=C\C(Cl)=O RJUIDDKTATZJFE-NSCUHMNNSA-N 0.000 abstract 3
- 159000000000 sodium salts Chemical class 0.000 abstract 3
- WGYKZJWCGVVSQN-UHFFFAOYSA-N Propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- YBBLOADPFWKNGS-UHFFFAOYSA-N 1,1-dimethylurea Chemical class CN(C)C(N)=O YBBLOADPFWKNGS-UHFFFAOYSA-N 0.000 abstract 1
- BOILZMXPEKUOGF-UHFFFAOYSA-N 2-(propylamino)butanoic acid Chemical compound CCCNC(CC)C(O)=O BOILZMXPEKUOGF-UHFFFAOYSA-N 0.000 abstract 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N Crotonic acid Chemical group C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 abstract 1
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 abstract 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N N-Propyl bromide Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000003047 N-acetyl group Chemical group 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N Phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N Sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 abstract 1
- MFBOGIVSZKQAPD-UHFFFAOYSA-M Sodium butyrate Chemical compound [Na+].CCCC([O-])=O MFBOGIVSZKQAPD-UHFFFAOYSA-M 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- 150000001805 chlorine compounds Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 abstract 1
- 238000007429 general method Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- WBGWGHYJIFOATF-UHFFFAOYSA-M potassium;methyl sulfate Chemical compound [K+].COS([O-])(=O)=O WBGWGHYJIFOATF-UHFFFAOYSA-M 0.000 abstract 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 abstract 1
- 230000001225 therapeutic Effects 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/006—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length of peptides containing derivatised side chain amino acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Analytical Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Acylated aliphatic N-monoalkyl amino carboxylic acid dimethylamides of the general formula R1R2N-CH.R-CO.N(CH3)2 wherein R represents a methyl, ethyl or isopropyl group, R1 represents the ethyl, n-propyl or sec. butyl group and R2 is an acetyl, propionyl or crotonyl group are prepared by the general methods described in the parent Specification. The products are stated to be new and have therapeutic properties. In the examples: (1) N-acetyl, propionyl and crotonyl-a -(n-propylamino) -n-butyric acid dimethylamides are prepared by acylation of a -(n-propylamino)-n-butyric acid dimethylamide, obtained by heating a -bromo-n-butyric acid dimethylamide with n-propylamine or by hydrogenating a -allylamino-butyric acid dimethylamide, with the acid chlorides and many other compounds of the above type prepared by this method are tabulated; (2) a -ethylamino- or n-propylamino-n-butyric acid is acylated with crotonyl chloride, converted into the acid chloride by means of phosphorus pentachloride and then reacted with dimethylamine; (3) a -(N-crotonyl propylamino) butyric acid sodium salt is reacted with dimethyl carbamic chloride; (4) ethyl-a -bromo-n-butyrate is reacted with n-propylamine, the product acylated with propionyl chloride, and then heated with dimethylamine; (5) crotonyl ethyl amide or crotonyl-n-propyl amide is heated in xylene with sodamide and the resulting sodium salt reacted with a -bromo-butyric acid dimethylamide; (6) a -amino-n-butyric acid dimethylamide is acylated with crotonyl chloride, the resulting N - crotonyl - a - amino - n - butyric acid dimethylamide converted into the sodium salt as in (5) and then reacted with propyl bromide; (7) a -ethylamino-n-butyramide is acylated with crotonyl chloride, converted into the sodium salt as in (5) and the product alkylated by means of potassium methyl sulphate.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB600893A true GB600893A (en) | 1948-04-21 |
Family
ID=1743284
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3303645A Expired GB600893A (en) | 1945-12-06 | Manufacture of acylated aliphatic amino carboxylic acid amides |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB600893A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2715119A (en) * | 1950-04-04 | 1955-08-09 | Boehringer Sohn Ingelheim | Preparation of amides |
-
1945
- 1945-12-06 GB GB3303645A patent/GB600893A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2715119A (en) * | 1950-04-04 | 1955-08-09 | Boehringer Sohn Ingelheim | Preparation of amides |
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