GB1409804A - Preparation of azetidinones - Google Patents
Preparation of azetidinonesInfo
- Publication number
- GB1409804A GB1409804A GB4189772A GB4189772A GB1409804A GB 1409804 A GB1409804 A GB 1409804A GB 4189772 A GB4189772 A GB 4189772A GB 4189772 A GB4189772 A GB 4189772A GB 1409804 A GB1409804 A GB 1409804A
- Authority
- GB
- United Kingdom
- Prior art keywords
- preparation
- aralkyl group
- group
- compounds
- alkali metal
- 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.)
- Expired
Links
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical class O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 title abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 150000004703 alkoxides Chemical class 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 229910001413 alkali metal ion Inorganic materials 0.000 abstract 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 239000012435 aralkylating agent Substances 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 125000002843 carboxylic acid group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C07D205/09—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4
- C07D205/095—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4 and with a nitrogen atom directly attached in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Abstract
1409804 Preparation of azetidinones BEECHAM GROUP Ltd 21 Aug 1973 [8 Sept 1972] 41897/72 Addition to 1269279 Heading C2C The invention comprises a process for the preparation of compounds of the general Formula III wherein R<SP>1</SP> is an optionally substituted alkyl, alkenyl, alkynyl or aralkyl group; R<SP>2</SP> is an esterified carboxylic acid group; R<SP>3</SP> is hydrogen or an aralkyl group and R<SP>4</SP> is an aralkyl group by reacting a compound of the Formula IIIA wherein R<SP>2</SP>, R<SP>3</SP>, and R<SP>4</SP> are as defined above in a substantially anhydrous liquid medium with a strong base selected from alkali metal hydroxides and C 1-6 alkoxides other than tertiary alkoxides, alkaline earth metal hydroxides and compounds of the formula where X<SP>+</SP> is an alkali metal ion, and with an alkylating, alkenylating, alkynylating or aralkylating agent to introduce the substituent R<SP>1</SP> onto the sulphur.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4189772A GB1409804A (en) | 1972-09-08 | 1972-09-08 | Preparation of azetidinones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4189772A GB1409804A (en) | 1972-09-08 | 1972-09-08 | Preparation of azetidinones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1409804A true GB1409804A (en) | 1975-10-15 |
Family
ID=10421863
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4189772A Expired GB1409804A (en) | 1972-09-08 | 1972-09-08 | Preparation of azetidinones |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1409804A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0020883A1 (en) * | 1979-04-03 | 1981-01-07 | Shionogi & Co., Ltd. | A process for preparing 3-beta-amino-4-beta-substituted 2-azetidinones and 3-(2,2-dihalogenovinyl)-imino-4-beta-substituted 2-azetidinone and 3-beta-(2,2-dihalogenovinyl)-amino-4-beta-substituted 2-azetidinone intermediates |
| US4855421A (en) * | 1984-07-13 | 1989-08-08 | Sanraku Incorporation | 2-Oxoazetidines, methods for their preparation, and their use |
-
1972
- 1972-09-08 GB GB4189772A patent/GB1409804A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0020883A1 (en) * | 1979-04-03 | 1981-01-07 | Shionogi & Co., Ltd. | A process for preparing 3-beta-amino-4-beta-substituted 2-azetidinones and 3-(2,2-dihalogenovinyl)-imino-4-beta-substituted 2-azetidinone and 3-beta-(2,2-dihalogenovinyl)-amino-4-beta-substituted 2-azetidinone intermediates |
| US4855421A (en) * | 1984-07-13 | 1989-08-08 | Sanraku Incorporation | 2-Oxoazetidines, methods for their preparation, and their use |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |