ZA847585B - Process for the manufacture of optically uniform azetidinones - Google Patents
Process for the manufacture of optically uniform azetidinonesInfo
- Publication number
- ZA847585B ZA847585B ZA847585A ZA847585A ZA847585B ZA 847585 B ZA847585 B ZA 847585B ZA 847585 A ZA847585 A ZA 847585A ZA 847585 A ZA847585 A ZA 847585A ZA 847585 B ZA847585 B ZA 847585B
- Authority
- ZA
- South Africa
- Prior art keywords
- lower alkyl
- signifies
- phenyl
- general formula
- benzyl
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
-
- 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
- C07D205/085—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 nitrogen atom directly attached in position 3
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Saccharide Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1. A process for the manufacture of optically uniform azetidinones of the general formula see diagramm : EP0138113,P5,F1 wherein R signifies benzyl, beta-(trimethylsilyl)-lower alkyl or beta-halo-lower alkyl, R**1 signifies a readily cleavable protecting group from the group consisting of benzyl, 2,4- or 3,4-di(lower alkoxy)benzyl, di[4-(lower alkoxy)phenyl]methyl, 4-(lower alkoxy)phenyl, lower 2-alkenyl and the group of the formula -CH2 -CH(OR**5)2 (a) or see diagramm : EP0138113,P5,F2 in which R**5 signifies lower alkyl and n signifies the number 0 or 1, R**2 signifies lower alkyl, phenyl-lower alkyl or lower alkoxyalkyl and R**3 signifies lower alkyl or phenyl-lower alkyl or R**2 and R**3 together with the centre of chirality and the oxygen atom signify a 5 or 6-membered 0-heterocycle which optionally contains a further oxygen atom not directly linked with the centre of chirality and which is optionally substituted by lower alkyl, lower alkoxy, oxo or spirocyclo-lower alkyl, and the residues denoted by lower have up to eight carbon atoms, characterized by reacting an alkali metal salt of a carboxylic acid of the general formula ROCONHCH2 COOH wherein R has the above significance, with an optically uniform compound of the general formula see diagramm : EP0138113,P6,F3 wherein R**1, R**2 and R**3 have the above significance, in the presence of a base and a sulphonic acid chloride of the general formula R**4-SO2 -Cl wherein R**4 signifies phenyl, lower alkylphenyl, halophenyl, lower alkyl or halo-lower alkyl, whereby the reaction is carried out in an anhydrous inert organic solvent at a temperature in the range of about -30 degrees C to about 50 degrees C.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH536583 | 1983-10-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA847585B true ZA847585B (en) | 1985-05-29 |
Family
ID=4292341
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA847585A ZA847585B (en) | 1983-10-03 | 1984-09-26 | Process for the manufacture of optically uniform azetidinones |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP0138113B1 (en) |
| JP (1) | JPS6092263A (en) |
| KR (1) | KR850003392A (en) |
| CN (1) | CN85100624A (en) |
| AT (1) | ATE33830T1 (en) |
| AU (1) | AU572194B2 (en) |
| CA (1) | CA1251455A (en) |
| DE (1) | DE3470736D1 (en) |
| DK (1) | DK411384A (en) |
| IL (1) | IL73089A (en) |
| NZ (1) | NZ209684A (en) |
| PH (1) | PH19418A (en) |
| ZA (1) | ZA847585B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60139667A (en) * | 1983-12-27 | 1985-07-24 | Takeda Chem Ind Ltd | Preparation of azetidinone |
| US4983732A (en) * | 1987-07-31 | 1991-01-08 | Eli Lilly And Company | Method of deprotection of 3-amino azetidinones |
| US5142039A (en) * | 1987-07-31 | 1992-08-25 | Eli Lilly And Company | β-lactam antibiotics |
| JPS6463567A (en) * | 1987-07-31 | 1989-03-09 | Lilly Co Eli | Deprotection of 3-aminoazetidinones |
| US5239068A (en) * | 1987-07-31 | 1993-08-24 | Eli Lilly And Company | Bicyclic β-lactam antibiotics |
| CN112175173B (en) * | 2020-10-09 | 2022-04-19 | 中国科学技术大学 | Preparation method of degradable poly-alpha-olefin material with controllable olefin insertion rate |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1262128A (en) * | 1981-08-27 | 1989-10-03 | Christian N. Hubschwerlen | .beta.-lactams |
| CA1251454A (en) * | 1983-01-20 | 1989-03-21 | Gerard Schmid | PROCESS FOR THE MANUFACTURE OF .beta.-LACTAMES |
| DK36784A (en) * | 1983-02-25 | 1984-08-26 | Hoffmann La Roche | PROCEDURE FOR PREPARING CHIRAL ALDEHYDES |
| JPS60139667A (en) * | 1983-12-27 | 1985-07-24 | Takeda Chem Ind Ltd | Preparation of azetidinone |
-
1984
- 1984-08-28 DK DK411384A patent/DK411384A/en not_active Application Discontinuation
- 1984-09-04 CA CA000462331A patent/CA1251455A/en not_active Expired
- 1984-09-26 IL IL73089A patent/IL73089A/en unknown
- 1984-09-26 DE DE8484111448T patent/DE3470736D1/en not_active Expired
- 1984-09-26 EP EP84111448A patent/EP0138113B1/en not_active Expired
- 1984-09-26 ZA ZA847585A patent/ZA847585B/en unknown
- 1984-09-26 AT AT84111448T patent/ATE33830T1/en not_active IP Right Cessation
- 1984-09-26 NZ NZ209684A patent/NZ209684A/en unknown
- 1984-09-28 AU AU33705/84A patent/AU572194B2/en not_active Ceased
- 1984-09-28 PH PH31277A patent/PH19418A/en unknown
- 1984-10-02 JP JP59205690A patent/JPS6092263A/en active Pending
- 1984-10-02 KR KR1019840006096A patent/KR850003392A/en not_active Application Discontinuation
-
1985
- 1985-04-01 CN CN198585100624A patent/CN85100624A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AU572194B2 (en) | 1988-05-05 |
| DE3470736D1 (en) | 1988-06-01 |
| IL73089A0 (en) | 1984-12-31 |
| CA1251455A (en) | 1989-03-21 |
| DK411384D0 (en) | 1984-08-28 |
| ATE33830T1 (en) | 1988-05-15 |
| AU3370584A (en) | 1985-04-18 |
| CN85100624A (en) | 1986-07-09 |
| EP0138113B1 (en) | 1988-04-27 |
| IL73089A (en) | 1988-02-29 |
| DK411384A (en) | 1985-04-04 |
| KR850003392A (en) | 1985-06-17 |
| EP0138113A1 (en) | 1985-04-24 |
| PH19418A (en) | 1986-04-10 |
| NZ209684A (en) | 1987-08-31 |
| JPS6092263A (en) | 1985-05-23 |
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