IL42843A - 1h-tetrazole-1-acetic acid and esters and processes for their preparation - Google Patents
1h-tetrazole-1-acetic acid and esters and processes for their preparationInfo
- Publication number
- IL42843A IL42843A IL42843A IL4284373A IL42843A IL 42843 A IL42843 A IL 42843A IL 42843 A IL42843 A IL 42843A IL 4284373 A IL4284373 A IL 4284373A IL 42843 A IL42843 A IL 42843A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- alkali metal
- formula
- tetrazole
- alkyl
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims abstract 10
- 238000000034 method Methods 0.000 title claims 9
- GRWAIJBHBCCLGS-UHFFFAOYSA-N 2-(tetrazol-1-yl)acetic acid Chemical compound OC(=O)CN1C=NN=N1 GRWAIJBHBCCLGS-UHFFFAOYSA-N 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 claims abstract 17
- -1 hydrocarbon radical Chemical class 0.000 claims abstract 13
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract 9
- 239000002253 acid Substances 0.000 claims abstract 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 7
- 150000007513 acids Chemical class 0.000 claims abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 5
- 239000001257 hydrogen Substances 0.000 claims abstract 5
- 125000003944 tolyl group Chemical group 0.000 claims abstract 4
- 125000005023 xylyl group Chemical group 0.000 claims abstract 4
- XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical compound [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims abstract 3
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 claims abstract 2
- PPXUUPXQWDQNGO-UHFFFAOYSA-N 2-azidoacetic acid Chemical compound OC(=O)CN=[N+]=[N-] PPXUUPXQWDQNGO-UHFFFAOYSA-N 0.000 claims abstract 2
- 230000001476 alcoholic effect Effects 0.000 claims abstract 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 2
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims abstract 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- BUYJAQOVJGKBEZ-UHFFFAOYSA-N 2-(5-ethoxycarbonyltetrazol-1-yl)acetic acid Chemical compound CCOC(=O)C1=NN=NN1CC(O)=O BUYJAQOVJGKBEZ-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 2
- MSMGXWFHBSCQFB-UHFFFAOYSA-N ethyl cyanoformate Chemical compound CCOC(=O)C#N MSMGXWFHBSCQFB-UHFFFAOYSA-N 0.000 claims 2
- 150000002431 hydrogen Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- QQULZKDKXRNHNB-UHFFFAOYSA-N 1-(carboxymethyl)tetrazole-5-carboxylic acid Chemical compound OC(=O)CN1N=NN=C1C(O)=O QQULZKDKXRNHNB-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- GJQBHOAJJGIPRH-UHFFFAOYSA-N benzoyl cyanide Chemical compound N#CC(=O)C1=CC=CC=C1 GJQBHOAJJGIPRH-UHFFFAOYSA-N 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- UNDCGJBEVRCWCU-UHFFFAOYSA-N ethyl 2-(5-benzoyltetrazol-1-yl)acetate Chemical compound CCOC(=O)CN1N=NN=C1C(=O)C1=CC=CC=C1 UNDCGJBEVRCWCU-UHFFFAOYSA-N 0.000 claims 1
- HVJJYOAPXBPQQV-UHFFFAOYSA-N ethyl 2-azidoacetate Chemical compound CCOC(=O)CN=[N+]=[N-] HVJJYOAPXBPQQV-UHFFFAOYSA-N 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 4
- 229930195733 hydrocarbon Natural products 0.000 abstract 4
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 150000002430 hydrocarbons Chemical class 0.000 abstract 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 1
- 125000006564 (C4-C8) cycloalkyl group Chemical group 0.000 abstract 1
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 abstract 1
- 150000001264 acyl cyanides Chemical class 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1435809 1 - H - Tetrazole - -1 - acetate esters and acids ELI LILLY & CO 13 Aug 1973 [14 Aug 1972] 38132/73 Heading C2C Novel tetrazolylacetate esters and acids having the general formula wherein R is a (C 1 -C 12 ) hydrocarbon radical free from aliphatic unsaturation, a (C 1 -C 12 ) hydrocarbon -O- radical free from aliphatic unsaturation or an -O- alkali metal radical; and R<SP>1</SP> is hydrogen, an alkali metal cation or a (C 1 -C 12 ) alkyl, (C 4 -C 8 ) cycloalkyl, phenyl, behzyl, p-nitrophenyl, p-nitrobenzyl, 2,2,2-trichloroethyl or phenacyl radical, as well those compounds of the above formula wherein R<SP>1</SP> may also be tolyl, xylyl or phenylethyl, are prepared by reacting an acyl cyanide of the formula (II) with an azidoacetic acid or ester thereof having the formula (III) at a temperature of from 80‹ to 135‹ C. The resultant tetrazolylacetate ester may be further reacted with either (a) an alcoholic alkali metal hydroxide to form the corresponding alkali metal salt, (b) a base to remove the 5-acyl substituent and form the alkali metal salt of 1-tetrazoleacetic acid, provided that R is a (C 1 -C 12 ) hydrocarbon radical, or (c) with an acid to remove the 5-acyl substituent and form the 1-tetrazoleacetic acid, provided that R is a (C 1 -C 12 ) hydrocarbon -O- radical.
[GB1435809A]
Claims (20)
1. A process for preparing tetrazolylacetate esters or acids or alkaline metal salts of the formula wherein is a C.- to C, alkyl, C.- C, alkoxy, C. - C, . , 1 6 ' ' 1 6 " 4 6 -cycloalkyl, C4- C6~ cycloalkoxy, phenyl, tolyl, xylyl, benzyl, phenoxy, tolyloxy, xjrlyloxy, or benzyloxy; and R1 is hydrogen, Cj- to C^-alkyl, C^- to Cg-cycloalkyl, phenyl, phenylethyl, 2,2,2-trichloroethyl, or phenacyl, which comprises heating a mixture containing a compound of the formula 0 II R-C-CN wherein R is as defined above, and a compound of the formula N3-CH2-C00R' wherein R1 is as defined above, at a temperature of from about 80 to about 135eC. for a time sufficient to form the tetra-zoleacetate ester or acid.
2. The process of Claim 1 wherein a compound of the formula 0 II R-C-CN and a compound of the formula 0 II N3-CH^-C-0R' 42843/2 are heated in an inert solvent.
3. The process of claims 1 or 2 wherein the tetrazolylacetate ester so obtained is reacted further with alcoholic alkali metal hydroxide to form the corresponding alkali metal salt.
4. The process of claims 1 or 2 wherein R is a S^- to C^- alkyiaxy, and R' is - to Cg-alkyl
5. The process of claim 4 wherein ethyl cyanoformate is reacted with ethyl azidpacetate to form ethyl 5-(ethoxycarbonyl) *·1Η- tetrazole -1 -acetate♦
6. The process of claims 1 or 2 wherein is a C^- to Cfi- alkyloxy, and R* is hydrogen.
7. The process of claim 6 wherein ethyl cyanoformate is reacted with azidoacetic acid to form 5-(ethoxycarbonyl) -lH-tetrazole-l-acetic acid.
8. The process of claims 1 or 2 wherein R is phenyl, and R' is a Cj to Cg- alkyl..
9. The process of claim 8 wherein benzoyl cyanid is reacted with ethyl azidoacetate to form ethyl 5 -benzoyl -lH-tetrazole-1 -acetate.
10. Compounds of the formula CH2C-0R' N wherein R is cyclo - alkoxy, phenyl, tolyl, xylyl, benzyl, phenoxy, tolyloxy, xylyloxy, benzyloxy, or -0-alkali metal; and R* is hydrogen, an alkali metal cation, C^- to C6-alkyl, phenyl, benzyl, p-nitrophenyl, p-nitrobenzyl, 2,2,2-trtchloroethyl, phenacyl, C4~C6 cycloalkyl, tolyl, xylyl, or phenylethyl. 42843/2
11. The compound of claim 10 wherein R is C^- to C^-alkyloxy and R' is C]- to Cg-alkyl.
12. The compound of claim 11 wherein the compound is ethyl 5 -(ethpxycarbonyl) -lH-tetrazole-l -acetate.
13. The compound of claim 10 wherein R is Cj- to C& alkyloxy and R' is hydrogen.
14. The compound of claim 13 wherein the compound is 5-(ethoxycarbonyl) -lH-tetrazole-l -acetic acid,
15. The compohd of claim 10 Wherein R is phenyl and R1 is Cj- to Cg-alkyl.
16. The compound of claim 15 wherein the compound is ethyl 5-benzoyl^-lH-tetrazole-l-acetate*
17. The compound of claim 10 wherein R is -O-alkali metal and R' is an alkali metal cation;
18. The compound of claim 17 Wherein the compound is the di -potassium salt of 5-carboxy-lH-tetrazole-1 -acetic acid.
19. A process for preparing tetrazolylacetate acids and esters of the formula R t o=c r 0 M-CH„-C-OR' '2 Wherein R and R' are as defined in claim 1, substantially as herein before described with particular reference to Examples 1 to 6.
20. Tetrazolylacetate acids, esters and salts of the formul R I 0=C ' r 0 N ^3™- 42843/2 wherein R and R* are as defined in claim 10, substantially as hereinbefore described with particular reference to Examples 1 to 7. S.HOROWITZ § Co} AGENTS FOR APPLICANTS
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28062572A | 1972-08-14 | 1972-08-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL42843A0 IL42843A0 (en) | 1976-01-30 |
| IL42843A true IL42843A (en) | 1976-12-31 |
Family
ID=23073908
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL42843A IL42843A (en) | 1972-08-14 | 1973-07-27 | 1h-tetrazole-1-acetic acid and esters and processes for their preparation |
Country Status (26)
| Country | Link |
|---|---|
| JP (1) | JPS5821628B2 (en) |
| KR (1) | KR780000071B1 (en) |
| AR (1) | AR195626A1 (en) |
| AT (1) | AT329555B (en) |
| AU (1) | AU476519B2 (en) |
| BE (1) | BE803520A (en) |
| BG (1) | BG21220A3 (en) |
| CA (1) | CA998397A (en) |
| CH (1) | CH588475A5 (en) |
| CS (1) | CS179425B2 (en) |
| DD (1) | DD110272A5 (en) |
| DE (1) | DE2340409A1 (en) |
| ES (1) | ES417837A1 (en) |
| FR (1) | FR2196336B1 (en) |
| GB (1) | GB1435809A (en) |
| HU (1) | HU166844B (en) |
| IE (1) | IE37949B1 (en) |
| IL (1) | IL42843A (en) |
| NL (1) | NL179380C (en) |
| PH (1) | PH10552A (en) |
| PL (1) | PL89385B1 (en) |
| RO (1) | RO73460A (en) |
| SE (1) | SE402913B (en) |
| SU (1) | SU576935A3 (en) |
| YU (1) | YU36513B (en) |
| ZA (1) | ZA735075B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2854015B2 (en) * | 1978-12-14 | 1980-10-09 | Dynamit Nobel Ag, 5210 Troisdorf | Process for the preparation of! H-TetrazoI-1-acetic acids and certain esters thereof |
| CN102341378B (en) | 2009-03-11 | 2015-09-09 | 日本曹达株式会社 | The preparation method of 1-alkyl-5-benzoyl-1H-TETRAZOLE derivative |
| CN114085193A (en) * | 2021-11-20 | 2022-02-25 | 九江中星医药化工有限公司 | Method for preparing 1H-tetrazoleacetic acid and derivatives thereof by aqueous phase method |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD70880A (en) * |
-
1973
- 1973-07-25 ZA ZA00735075A patent/ZA735075B/en unknown
- 1973-07-25 IE IE1268/73A patent/IE37949B1/en unknown
- 1973-07-26 AU AU58575/73A patent/AU476519B2/en not_active Expired
- 1973-07-27 IL IL42843A patent/IL42843A/en unknown
- 1973-08-02 CA CA177,995A patent/CA998397A/en not_active Expired
- 1973-08-03 PH PH14880A patent/PH10552A/en unknown
- 1973-08-07 YU YU02148/73A patent/YU36513B/en unknown
- 1973-08-09 DE DE19732340409 patent/DE2340409A1/en active Granted
- 1973-08-10 AT AT703773A patent/AT329555B/en not_active IP Right Cessation
- 1973-08-10 HU HUEI490A patent/HU166844B/hu unknown
- 1973-08-10 BE BE1005292A patent/BE803520A/en unknown
- 1973-08-13 KR KR7301319A patent/KR780000071B1/en not_active Expired
- 1973-08-13 SU SU7301955734A patent/SU576935A3/en active
- 1973-08-13 PL PL1973164647A patent/PL89385B1/pl unknown
- 1973-08-13 SE SE7311051A patent/SE402913B/en unknown
- 1973-08-13 GB GB3813273A patent/GB1435809A/en not_active Expired
- 1973-08-13 ES ES417837A patent/ES417837A1/en not_active Expired
- 1973-08-14 FR FR7329649A patent/FR2196336B1/fr not_active Expired
- 1973-08-14 DD DD172890A patent/DD110272A5/xx unknown
- 1973-08-14 RO RO7375793A patent/RO73460A/en unknown
- 1973-08-14 NL NLAANVRAGE7311222,A patent/NL179380C/en not_active IP Right Cessation
- 1973-08-14 AR AR249586A patent/AR195626A1/en active
- 1973-08-14 BG BG024317A patent/BG21220A3/en unknown
- 1973-08-14 CS CS7300005736A patent/CS179425B2/en unknown
- 1973-08-14 JP JP48091225A patent/JPS5821628B2/en not_active Expired
- 1973-08-14 CH CH1171373A patent/CH588475A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL179380C (en) | 1986-09-01 |
| CA998397A (en) | 1976-10-12 |
| IL42843A0 (en) | 1976-01-30 |
| AU5857573A (en) | 1975-01-30 |
| BG21220A3 (en) | 1976-03-20 |
| DE2340409C2 (en) | 1988-03-17 |
| ZA735075B (en) | 1975-03-26 |
| FR2196336B1 (en) | 1977-02-25 |
| RO73460A (en) | 1982-09-09 |
| AT329555B (en) | 1976-05-25 |
| JPS4975580A (en) | 1974-07-20 |
| DE2340409A1 (en) | 1974-02-28 |
| ATA703773A (en) | 1975-08-15 |
| PL89385B1 (en) | 1976-11-30 |
| NL7311222A (en) | 1974-02-18 |
| CH588475A5 (en) | 1977-06-15 |
| AR195626A1 (en) | 1973-10-23 |
| IE37949B1 (en) | 1977-11-23 |
| ES417837A1 (en) | 1976-02-16 |
| YU214873A (en) | 1982-02-25 |
| KR780000071B1 (en) | 1978-03-30 |
| GB1435809A (en) | 1976-05-19 |
| IE37949L (en) | 1974-02-14 |
| SU576935A3 (en) | 1977-10-15 |
| HU166844B (en) | 1975-06-28 |
| SE402913B (en) | 1978-07-24 |
| FR2196336A1 (en) | 1974-03-15 |
| AU476519B2 (en) | 1976-09-23 |
| BE803520A (en) | 1974-02-11 |
| CS179425B2 (en) | 1977-10-31 |
| DD110272A5 (en) | 1974-12-12 |
| JPS5821628B2 (en) | 1983-05-02 |
| PH10552A (en) | 1977-06-08 |
| YU36513B (en) | 1984-02-29 |
| NL179380B (en) | 1986-04-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| IL42843A (en) | 1h-tetrazole-1-acetic acid and esters and processes for their preparation | |
| IL86941A (en) | Process for the preparation of cephem compounds and some new cephalosporin derivatives prepared by this process | |
| US2449191A (en) | Phenacetylaminomethylcrotonic acid | |
| GB1297299A (en) | ||
| ES472821A1 (en) | Process for preparing optically active unsubstituted or substituted 2-amino-2-phenyl-acetic acids. | |
| ES8304115A1 (en) | Process for Preparing Gamma- butyrothiolactone Derivatives and Intermediates Therefor | |
| US2440355A (en) | Process and culture media for producing penicillin | |
| ES8403124A1 (en) | Process for the preparation of vincaminic acid esters | |
| GB1580482A (en) | 7-amino-3-(sulphoalkyl-1,3,4-oxadiazol-2-yl)-thiomethyl-3-cephem-4-carboxylic acid derivatives | |
| GB1439898A (en) | Method of preparing substituted cephalosporins and penicillins | |
| US3773757A (en) | Process for the preparation of alpha-carboxyarylmethyl-and alpha-carboaryloxy-arylmethyl penicillins | |
| US2440361A (en) | Process and culture media for the production of penicillin | |
| GB1439378A (en) | ||
| US3017423A (en) | Organic compounds and process | |
| GB846737A (en) | 3-substituted 4-hydroxybenzoic acids and their preparation | |
| SU462830A1 (en) | The method of obtaining phosphorus-containing 1-phenyl-5-methyltriazole-1,2,3 | |
| GB1031544A (en) | Improvements in or relating to phthalimides | |
| DE3263875D1 (en) | Process for preparing hydrazidines | |
| GB1414324A (en) | Process for preparing 7-acylamino-3-substituted-3-cephem-4- carboxylic acid derivatives | |
| GB1390556A (en) | Process for the preparation of methyl thionophosphonic acid esters | |
| GB1365954A (en) | Process for acetylation | |
| GB613489A (en) | Improvements in process and culture medium for the production of penicillin | |
| JPS5663973A (en) | Novel thiadiazol-5-ylthiol ester and its preparation | |
| GB1242185A (en) | Preparation of (cis-1,2-epoxypropyl)phosphonic acid and salts and esters thereof | |
| GB1455004A (en) | Process for the preparation of 2-pyrrolidinone and 2-pyrrolinone derivatives |