JPS5569548A - Optically active alpha-acylamino-gamma-formylbutyric acid ester - Google Patents
Optically active alpha-acylamino-gamma-formylbutyric acid esterInfo
- Publication number
- JPS5569548A JPS5569548A JP14233278A JP14233278A JPS5569548A JP S5569548 A JPS5569548 A JP S5569548A JP 14233278 A JP14233278 A JP 14233278A JP 14233278 A JP14233278 A JP 14233278A JP S5569548 A JPS5569548 A JP S5569548A
- Authority
- JP
- Japan
- Prior art keywords
- optically active
- acylamino
- formula
- acid ester
- compound
- 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
- 150000001875 compounds Chemical class 0.000 abstract 3
- -1 etc. Chemical group 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 2
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 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
- 239000006035 Tryptophane Substances 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001413 amino acids Chemical class 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 238000010531 catalytic reduction reaction Methods 0.000 abstract 1
- 239000012024 dehydrating agents Substances 0.000 abstract 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 229910052987 metal hydride Inorganic materials 0.000 abstract 1
- 150000004681 metal hydrides Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 230000009257 reactivity Effects 0.000 abstract 1
- 238000006722 reduction reaction Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 229960004799 tryptophan Drugs 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
NEW MATERIAL:An optically active α-acylamino-γ-formylbutyric acid ester of formula I (R1 is acyl such as acetyl, benzoyl, formyl, etc.; R2 is alkyl such as methyl, ethyl, propyl, etc., aromatic group such as phenyl, benzyl, etc., or aralkyl, etc.).
EXAMPLE: L-α-Acetamino-γ-formylbutyric acid methyl ester.
USE: Intermediate of optically active amino acids. Optically active tryptophane is prepared from the title compound in high reactivity and yield. Since the compound has well known chemical properties and high stability, it can be easily treated in an industrial scale.
PROCESS: The optically active α-acylamino-γ-cyanobutyric acid ester of formula III is prepared by reacting acylglutamin ester of formula II with a dehydrating agent. The compound III is converted to the compound of formula I by the catalytic reduction or by the reduction with a metal hydride such as diborane.
COPYRIGHT: (C)1980,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14233278A JPS5569548A (en) | 1978-11-20 | 1978-11-20 | Optically active alpha-acylamino-gamma-formylbutyric acid ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14233278A JPS5569548A (en) | 1978-11-20 | 1978-11-20 | Optically active alpha-acylamino-gamma-formylbutyric acid ester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS5569548A true JPS5569548A (en) | 1980-05-26 |
Family
ID=15312882
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14233278A Pending JPS5569548A (en) | 1978-11-20 | 1978-11-20 | Optically active alpha-acylamino-gamma-formylbutyric acid ester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5569548A (en) |
-
1978
- 1978-11-20 JP JP14233278A patent/JPS5569548A/en active Pending
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