JPS55136279A - Preparation of tryptophan hydantoin - Google Patents
Preparation of tryptophan hydantoinInfo
- Publication number
- JPS55136279A JPS55136279A JP4272679A JP4272679A JPS55136279A JP S55136279 A JPS55136279 A JP S55136279A JP 4272679 A JP4272679 A JP 4272679A JP 4272679 A JP4272679 A JP 4272679A JP S55136279 A JPS55136279 A JP S55136279A
- Authority
- JP
- Japan
- Prior art keywords
- phenylhydrazine
- aqueous medium
- formula
- formylethylhydantoin
- 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.)
- Pending
Links
- QIVBCDIJIAJPQS-SECBINFHSA-N D-tryptophane Chemical compound C1=CC=C2C(C[C@@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-SECBINFHSA-N 0.000 title abstract 2
- WJRBRSLFGCUECM-UHFFFAOYSA-N Hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 title 1
- 229940091173 hydantoin Drugs 0.000 title 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 4
- HKOOXMFOFWEVGF-UHFFFAOYSA-N Phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 abstract 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 4
- 229940067157 phenylhydrazine Drugs 0.000 abstract 4
- DZRABPWQOOXACE-UHFFFAOYSA-N 3-(2,5-dioxoimidazolidin-4-yl)propanal Chemical compound O=CCCC1NC(=O)NC1=O DZRABPWQOOXACE-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
Abstract
PURPOSE: To prepare the title compound useful as an intermediate for tryptophan, in one stage in high yield and purity, by reacting phenylhydrazine with 5-formylethylhydantoin in an acid aqueous medium under heating.
CONSTITUTION: 5-Formylethylhydantoin (F) of formula I is reacted with phenylhydrazine of formula II in an aqueous medium, preferably hydrochloric acid or aqueous sulfuric acid, under heating at 80 to the reflux temperature to give the compound of formula III. Preferably, the molar concentration of free hydrochloric or sulfuric acid is 0.5 or less, and the F solution is added dropwise slowly to a phenylhydrazine solution.
EFFECT: The aqueous medium provides safety, easy control of reaction temperature, operation, and a reduction in amount of phenylhydrazine.
COPYRIGHT: (C)1980,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4272679A JPS55136279A (en) | 1979-04-09 | 1979-04-09 | Preparation of tryptophan hydantoin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4272679A JPS55136279A (en) | 1979-04-09 | 1979-04-09 | Preparation of tryptophan hydantoin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS55136279A true JPS55136279A (en) | 1980-10-23 |
Family
ID=12644059
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4272679A Pending JPS55136279A (en) | 1979-04-09 | 1979-04-09 | Preparation of tryptophan hydantoin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS55136279A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0052199A1 (en) * | 1980-11-15 | 1982-05-26 | Degussa Aktiengesellschaft | Process for producing tryptophane hydantoin |
| WO2016094846A1 (en) * | 2014-12-11 | 2016-06-16 | President And Fellows Of Harvard College | Inhibitors of cellular necrosis and related methods |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5028958A (en) * | 1973-07-16 | 1975-03-24 |
-
1979
- 1979-04-09 JP JP4272679A patent/JPS55136279A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5028958A (en) * | 1973-07-16 | 1975-03-24 |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0052199A1 (en) * | 1980-11-15 | 1982-05-26 | Degussa Aktiengesellschaft | Process for producing tryptophane hydantoin |
| DE3043259A1 (en) * | 1980-11-15 | 1982-06-03 | Degussa Ag, 6000 Frankfurt | METHOD FOR PRODUCING TRYPTOPHANE HYDANTOIN |
| US4374995A (en) * | 1980-11-15 | 1983-02-22 | Degussa Aktiengesellschaft | Process for the production of tryptophane-hydantoin |
| WO2016094846A1 (en) * | 2014-12-11 | 2016-06-16 | President And Fellows Of Harvard College | Inhibitors of cellular necrosis and related methods |
| US9499521B2 (en) | 2014-12-11 | 2016-11-22 | President And Fellows Of Harvard College | Inhibitors of cellular necrosis and related methods |
| US9944628B2 (en) | 2014-12-11 | 2018-04-17 | President And Fellows Of Harvard College | Inhibitors of cellular necrosis and related methods |
| US10508102B2 (en) | 2014-12-11 | 2019-12-17 | President And Fellows Of Harvard College | Inhibitors of cellular necrosis and related methods |
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