SU345161A1 - METHOD FOR OBTAINING AMINO ACID DERIVATIVES - Google Patents
METHOD FOR OBTAINING AMINO ACID DERIVATIVESInfo
- Publication number
- SU345161A1 SU345161A1 SU1482767A SU1482767A SU345161A1 SU 345161 A1 SU345161 A1 SU 345161A1 SU 1482767 A SU1482767 A SU 1482767A SU 1482767 A SU1482767 A SU 1482767A SU 345161 A1 SU345161 A1 SU 345161A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- amino acid
- acid derivatives
- obtaining amino
- benzotriazole
- obtaining
- Prior art date
Links
- 150000003862 amino acid derivatives Chemical class 0.000 title description 3
- 150000001412 amines Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- MTEKRZYXGMSPFX-UHFFFAOYSA-N 2-(2H-benzotriazol-4-ylamino)acetic acid Chemical compound OC(=O)CNC1=CC=CC2=C1N=NN2 MTEKRZYXGMSPFX-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- 150000003977 halocarboxylic acids Chemical class 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- ZDWPBMJZDNXTPG-UHFFFAOYSA-N 2H-benzotriazol-4-amine Chemical compound NC1=CC=CC2=C1NN=N2 ZDWPBMJZDNXTPG-UHFFFAOYSA-N 0.000 description 1
- 229940100197 ANTIMETABOLITES Drugs 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L Copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 230000000340 anti-metabolite Effects 0.000 description 1
- 239000002256 antimetabolite Substances 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 150000001565 benzotriazoles Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- -1 ketomalonic acid o-aminophenyl hydrazone Chemical compound 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
Description
Изобретение относитс к способу получени нового, не описанного в литературе типа соединений в р ду бензотриазола с аминным типом св зи между аминокислотой и гетероциклическим основанием, которые обладают биологической активностью и могут найти применение в медицине.This invention relates to a method for producing a new, not described in the literature, type of compounds in the benzotriazole series with an amine type of bond between an amino acid and a heterocyclic base, which have biological activity and can be used in medicine.
Известен способ получени бензотриазола путем взаимодействи о-аминофенилгидразона кетомалоновой кислоты с аммиачны.м раствором сульфата меди при нагревании. Однако в литературе отсутствуют сведени о снособа .х получени аминокислотных нроизводны.х бензотриазола с аминным типом св зи между аминокислотой и гетероциклом.A known method for producing benzotriazole is by reacting ketomalonic acid o-aminophenyl hydrazone with ammoniacal copper sulfate solution with heating. However, there are no references in the literature about the ways of obtaining amino acid derivatives of benzotriazole with the amine type of bond between the amino acid and the heterocycle.
С целью получеии указаиных соединений предлагаетс способ получени новых антиметаболитов нуклеинобелкового обмена-аминокислотных производных бензотриазола с аминным типом св зи, заключающийс во взаимодействии 4-аминобензотриазола с натриевой солью соответствующей галоидкарбоновой кислоты при нагревании с последующи.м выделением целевого продукта известным способом .For the purpose of obtaining the above compounds, a method is proposed for the preparation of new antimetabolites of nucleobrotein exchange-amino acid derivatives of benzotriazole with an amine type of bond, which consists in the interaction of 4-aminobenzotriazole with the sodium salt of the corresponding halocarboxylic acid when heated with subsequent m.
Пример. Получение 4-бензотриазолилглицина .Example. Getting 4-benzotriazolylglycine.
триазола. Полученную смесь кип т т 2 час. При охлаждении реакционной смесн бепзотриазолилглицин осаждаетс в виде масла, которое быстро кристаллизуетс . Продукт реакции отфильтровывают, промывают водой и сущат. Получают 3,67 г (73%) 4-бензотриазолилглицина в виде светло-желтых игл, т. пл. 215-217°С с разложением (из ацетона).triazole. The resulting mixture was boiled for 2 hours. When cooling the reaction mixture, bepzotriazolylglycine precipitates as an oil, which quickly crystallizes. The reaction product is filtered off, washed with water and a solid. 3.67 g (73%) of 4-benzotriazolylglycine are obtained in the form of light yellow needles, mp. 215-217 ° С with decomposition (from acetone).
iRf 0,15 (система н-бутанол, насыщенный водой ), 0,33 (вода, насыщенна н-бутаполом), 0,52 (н-бутапол, уксусна кислота, вода в соотношенин ). УФ-спектр: Хмакс 228 нм (Ige 4,36), 272 нм (Ige 3,54), 318 нм (Ige 3,81).iRf 0.15 (system n-butanol saturated with water), 0.33 (water saturated with n-butapol), 0.52 (n-butapol, acetic acid, water by ratio). UV spectrum: Hmax 228 nm (Ige 4.36), 272 nm (Ige 3.54), 318 nm (Ige 3.81).
Найдено, %: N 29,26, 29,15.Found,%: N 29.26, 29.15.
CsH8N.,0..CsH8N., 0 ..
Мол. вес 192,18.Mol weight 192.18.
Вычнслено, %: N 29,16.Calcd.,%: N 29.16.
Предмет изобретени Subject invention
Способ получени аминокислотных производных бензотриазола с аминным типом св зи .между аминокислотой и гетероциклом, отличающийс тем, что 4-аминобензотрпазол подвергают взаимодействию с натриевой солью соответствующей галоидкарбоновой кислоты при нагреванни с последующим выделеA method for producing amino acid derivatives of benzotriazole with an amine type of bond. Between an amino acid and a heterocycle, characterized in that 4-aminobenzotrpazole is reacted with the sodium salt of the corresponding halocarboxylic acid when heated, followed by separation
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU345161A1 true SU345161A1 (en) |
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