DE2126765A1 - Verfahren zur Herstellung von N-Acyltryptophan aus Alkylestern der 2-Acylamido-2-carbalkoxy-2-(beta-indolyl)-propansäure - Google Patents
Verfahren zur Herstellung von N-Acyltryptophan aus Alkylestern der 2-Acylamido-2-carbalkoxy-2-(beta-indolyl)-propansäureInfo
- Publication number
- DE2126765A1 DE2126765A1 DE19712126765 DE2126765A DE2126765A1 DE 2126765 A1 DE2126765 A1 DE 2126765A1 DE 19712126765 DE19712126765 DE 19712126765 DE 2126765 A DE2126765 A DE 2126765A DE 2126765 A1 DE2126765 A1 DE 2126765A1
- Authority
- DE
- Germany
- Prior art keywords
- indolyl
- acylamido
- propanoic acid
- acyltryptophan
- carboxy
- 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
- 238000000034 method Methods 0.000 title claims description 8
- 125000005907 alkyl ester group Chemical group 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 17
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 11
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 11
- 235000019260 propionic acid Nutrition 0.000 claims description 10
- 230000020477 pH reduction Effects 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 6
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 6
- 238000006114 decarboxylation reaction Methods 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 238000002425 crystallisation Methods 0.000 claims description 3
- 230000008025 crystallization Effects 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- QIVBCDIJIAJPQS-UHFFFAOYSA-N tryptophan Chemical compound C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 3
- DZTHIGRZJZPRDV-LBPRGKRZSA-N N-acetyl-L-tryptophan Chemical group C1=CC=C2C(C[C@H](NC(=O)C)C(O)=O)=CNC2=C1 DZTHIGRZJZPRDV-LBPRGKRZSA-N 0.000 description 3
- DZTHIGRZJZPRDV-UHFFFAOYSA-N Nalpha-Acetyltryptophan Natural products C1=CC=C2C(CC(NC(=O)C)C(O)=O)=CNC2=C1 DZTHIGRZJZPRDV-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000002475 indoles Chemical class 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 229940116191 n-acetyltryptophan Drugs 0.000 description 3
- 230000006378 damage Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RNEMLJPSSOJRHX-NSHDSACASA-N (2s)-2-formamido-3-(1h-indol-3-yl)propanoic acid Chemical compound C1=CC=C2C(C[C@@H](C(=O)O)NC=O)=CNC2=C1 RNEMLJPSSOJRHX-NSHDSACASA-N 0.000 description 1
- SOWXHUICOFYUDQ-UHFFFAOYSA-N 2-(1h-indol-2-yl)propanoic acid Chemical compound C1=CC=C2NC(C(C(O)=O)C)=CC2=C1 SOWXHUICOFYUDQ-UHFFFAOYSA-N 0.000 description 1
- -1 2-acetamido-2-carboxy-3- (-indolyl) -propanoic acid Chemical compound 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
- 150000001371 alpha-amino acids Chemical class 0.000 description 1
- 235000008206 alpha-amino acids Nutrition 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS376970A CS152222B1 (enExample) | 1970-05-29 | 1970-05-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2126765A1 true DE2126765A1 (de) | 1971-12-09 |
Family
ID=5378724
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712126765 Pending DE2126765A1 (de) | 1970-05-29 | 1971-05-28 | Verfahren zur Herstellung von N-Acyltryptophan aus Alkylestern der 2-Acylamido-2-carbalkoxy-2-(beta-indolyl)-propansäure |
Country Status (3)
| Country | Link |
|---|---|
| CS (1) | CS152222B1 (enExample) |
| DE (1) | DE2126765A1 (enExample) |
| GB (1) | GB1343675A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4073795A (en) | 1976-06-22 | 1978-02-14 | Hoffmann-La Roche Inc. | Synthesis of tryptophans |
| US4316847A (en) * | 1979-07-30 | 1982-02-23 | Hoffmann-La Roche Inc. | Pyrroles and pyrrolidines |
-
1970
- 1970-05-29 CS CS376970A patent/CS152222B1/cs unknown
-
1971
- 1971-05-28 DE DE19712126765 patent/DE2126765A1/de active Pending
- 1971-05-28 GB GB1806871A patent/GB1343675A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1343675A (en) | 1974-01-16 |
| CS152222B1 (enExample) | 1973-12-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHW | Rejection |