GB723986A - Preparation of n-acyltryptophan esters - Google Patents
Preparation of n-acyltryptophan estersInfo
- Publication number
- GB723986A GB723986A GB3002051A GB3002051A GB723986A GB 723986 A GB723986 A GB 723986A GB 3002051 A GB3002051 A GB 3002051A GB 3002051 A GB3002051 A GB 3002051A GB 723986 A GB723986 A GB 723986A
- Authority
- GB
- United Kingdom
- Prior art keywords
- esters
- indolyl
- methyl
- acid
- aceto
- 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
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/20—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals substituted additionally by nitrogen atoms, e.g. tryptophane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Abstract
N-Acyltrotophan esters are prepared by treating an ester of a -acyl-b -(3-indolyl)-propionic acid with hydrazoic acid and sulphuric acid. The esters so produced may then be hydrolysed, preferably in alkaline solution to yield tryptophan. In examples: (1) ethyl a - aceto - b - (3 - indolyl) - propionate in chloroform is mixed with hydrazoic acid and added dropwise to a cooled stirred mixture of concentrated sulphuric acid and chloroform to yield N-acetyltryptophan ethyl ester, which upon hydrolysis with aqueous sodium hydroxide gives tryptophan; (2) as in (1) replacing the ethyl ester by the corresponding methyl derivative. Reference is made to the N-benzoyltryptophan esters. Methyl a -aceto-b -(3-indolyl)-propionate is prepared from methyl acetoacetate and gramine by condensation using sodium ethoxide, followed by treatment with methyl sulphate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3002051A GB723986A (en) | 1951-12-21 | 1951-12-21 | Preparation of n-acyltryptophan esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3002051A GB723986A (en) | 1951-12-21 | 1951-12-21 | Preparation of n-acyltryptophan esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB723986A true GB723986A (en) | 1955-02-16 |
Family
ID=10300968
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3002051A Expired GB723986A (en) | 1951-12-21 | 1951-12-21 | Preparation of n-acyltryptophan esters |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB723986A (en) |
-
1951
- 1951-12-21 GB GB3002051A patent/GB723986A/en not_active Expired
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