JPS5750958A - Preparation of tryptophan derivative - Google Patents
Preparation of tryptophan derivativeInfo
- Publication number
- JPS5750958A JPS5750958A JP12729280A JP12729280A JPS5750958A JP S5750958 A JPS5750958 A JP S5750958A JP 12729280 A JP12729280 A JP 12729280A JP 12729280 A JP12729280 A JP 12729280A JP S5750958 A JPS5750958 A JP S5750958A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- tryptophan
- phenylhydrazine
- indole
- 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-VIFPVBQESA-N L-tryptophane Chemical class C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 4
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 abstract 2
- 229940067157 phenylhydrazine Drugs 0.000 abstract 2
- 238000005978 reductive desulfurization reaction Methods 0.000 abstract 2
- -1 N- substituted glutamic acid Chemical class 0.000 abstract 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 238000006482 condensation reaction Methods 0.000 abstract 1
- 150000002430 hydrocarbons Chemical group 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 abstract 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
Landscapes
- Indole Compounds (AREA)
Abstract
PURPOSE: To obtain the titled compound which is an intermediate of tryptophan, easily, in high yield, by the reductive desulfurization of an easily producible N- substituted glutamic acid γ-thioester, followed by indole condensation reaction of the product with phenylhydrazine.
CONSTITUTION: The compound of formula I [R1 is R3CONH (R3 is H or hydrocarbon residue), R4OCONH (R4 is hydrocarbon residue), R4SO2NH, or amino protected with the group of formula II; R2 is lower alkyl, aralkyl or phenyl], is used as a raw material, and converted to the compound of formula III by reductive desulfurization. The objective tryptophan derivative of formula IV can be prepared by the indole-cyclization reaction of the compound of formula III with phenylhydrazine.
COPYRIGHT: (C)1982,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12729280A JPS5750958A (en) | 1980-09-16 | 1980-09-16 | Preparation of tryptophan derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12729280A JPS5750958A (en) | 1980-09-16 | 1980-09-16 | Preparation of tryptophan derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS5750958A true JPS5750958A (en) | 1982-03-25 |
Family
ID=14956347
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12729280A Pending JPS5750958A (en) | 1980-09-16 | 1980-09-16 | Preparation of tryptophan derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5750958A (en) |
-
1980
- 1980-09-16 JP JP12729280A patent/JPS5750958A/en active Pending
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