DE2521895A1 - Alpha-amino-2-adamantylessigsaeure und verfahren zu ihrer herstellung - Google Patents
Alpha-amino-2-adamantylessigsaeure und verfahren zu ihrer herstellungInfo
- Publication number
- DE2521895A1 DE2521895A1 DE19752521895 DE2521895A DE2521895A1 DE 2521895 A1 DE2521895 A1 DE 2521895A1 DE 19752521895 DE19752521895 DE 19752521895 DE 2521895 A DE2521895 A DE 2521895A DE 2521895 A1 DE2521895 A1 DE 2521895A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- adamantylacetic
- amino
- adamantylacetic acid
- alpha
- 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.)
- Ceased
Links
- QHBKDONXFKTUGL-UHFFFAOYSA-N 2-(2-adamantyl)-2-aminoacetic acid Chemical compound C1C(C2)CC3CC1C(C(N)C(O)=O)C2C3 QHBKDONXFKTUGL-UHFFFAOYSA-N 0.000 title claims abstract description 10
- KVBKBENCOHRLFW-UHFFFAOYSA-N 2-(2-adamantyl)acetic acid Chemical compound C1C(C2)CC3CC1C(CC(=O)O)C2C3 KVBKBENCOHRLFW-UHFFFAOYSA-N 0.000 title claims abstract description 10
- UPJKHWCBDDDTQS-UHFFFAOYSA-N 2-(2-adamantyl)-2-bromoacetic acid Chemical compound C1C(C2)CC3CC1C(C(Br)C(=O)O)C2C3 UPJKHWCBDDDTQS-UHFFFAOYSA-N 0.000 title claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 6
- SVDFXNCPIWMGLN-UHFFFAOYSA-N ethyl 2-(2-adamantyl)acetate Chemical compound C1C(C2)CC3CC1C(CC(=O)OCC)C2C3 SVDFXNCPIWMGLN-UHFFFAOYSA-N 0.000 claims abstract description 6
- -1 6-APA trimethylsilyl ester Chemical class 0.000 claims abstract description 5
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003708 ampul Substances 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 2
- 229940049954 penicillin Drugs 0.000 abstract description 5
- 229930182555 Penicillin Natural products 0.000 abstract description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract description 3
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 abstract description 3
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 2
- 239000007788 liquid Substances 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- GQBVPWDPTCICNW-UHFFFAOYSA-N 2-(1-adamantyl)-2-bromoacetic acid Chemical compound C1C(C2)CC3CC2CC1(C(Br)C(=O)O)C3 GQBVPWDPTCICNW-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/15—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing halogen
- C07C53/23—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing halogen containing rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| YU135274A YU36151B (en) | 1974-05-16 | 1974-05-16 | Process for preparing alpha-amino-2-adamantyl acetic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2521895A1 true DE2521895A1 (de) | 1976-04-08 |
Family
ID=25553813
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752521895 Ceased DE2521895A1 (de) | 1974-05-16 | 1975-05-16 | Alpha-amino-2-adamantylessigsaeure und verfahren zu ihrer herstellung |
Country Status (5)
| Country | Link |
|---|---|
| AT (1) | AT336563B (zh) |
| CH (1) | CH594603A5 (zh) |
| DE (1) | DE2521895A1 (zh) |
| SU (1) | SU585808A3 (zh) |
| YU (1) | YU36151B (zh) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2272825A3 (en) * | 2000-03-10 | 2011-05-04 | Bristol-Myers Squibb Company | N-Protected amino hydroxy adamantane carboxylic acid and process for its preparation |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104829444A (zh) * | 2014-02-12 | 2015-08-12 | 上海医药工业研究院 | 一种α-溴代三环[3.3.1.13,7]癸烷-1-乙酸的后处理方法 |
-
1974
- 1974-05-16 YU YU135274A patent/YU36151B/xx unknown
-
1975
- 1975-05-06 CH CH583975A patent/CH594603A5/xx not_active IP Right Cessation
- 1975-05-13 AT AT362775A patent/AT336563B/de not_active IP Right Cessation
- 1975-05-15 SU SU752136594A patent/SU585808A3/ru active
- 1975-05-16 DE DE19752521895 patent/DE2521895A1/de not_active Ceased
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2272825A3 (en) * | 2000-03-10 | 2011-05-04 | Bristol-Myers Squibb Company | N-Protected amino hydroxy adamantane carboxylic acid and process for its preparation |
| USRE44186E1 (en) | 2000-03-10 | 2013-04-30 | Bristol-Myers Squibb Company | Cyclopropyl-fused pyrrolidine-based inhibitors of dipeptidyl peptidase IV and method |
Also Published As
| Publication number | Publication date |
|---|---|
| CH594603A5 (zh) | 1978-01-13 |
| SU585808A3 (ru) | 1977-12-25 |
| YU135274A (en) | 1981-06-30 |
| YU36151B (en) | 1982-02-25 |
| ATA362775A (de) | 1976-09-15 |
| AT336563B (de) | 1977-05-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8131 | Rejection | ||
| 8128 | New person/name/address of the agent |
Representative=s name: VON FUENER, A., DIPL.-CHEM. DR.RER.NAT. EBBINGHAUS |