JPS565457A - Thienamycin intermediate - Google Patents
Thienamycin intermediateInfo
- Publication number
- JPS565457A JPS565457A JP8097379A JP8097379A JPS565457A JP S565457 A JPS565457 A JP S565457A JP 8097379 A JP8097379 A JP 8097379A JP 8097379 A JP8097379 A JP 8097379A JP S565457 A JPS565457 A JP S565457A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- hydroxyethyl
- thienamycin
- azetidinone
- prepare
- 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.)
- Pending
Links
- WKDDRNSBRWANNC-ATRFCDNQSA-N Thienamycin Chemical compound C1C(SCCN)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 WKDDRNSBRWANNC-ATRFCDNQSA-N 0.000 title abstract 3
- WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 title abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- MOKDVDXMMSCFHC-UHFFFAOYSA-N 1,1-dimethoxy-3-nitropropane Chemical compound COC(OC)CC[N+]([O-])=O MOKDVDXMMSCFHC-UHFFFAOYSA-N 0.000 abstract 1
- 238000003747 Grignard reaction Methods 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 150000002547 isoxazolines Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- MCVVUJPXSBQTRZ-ONEGZZNKSA-N methyl (e)-but-2-enoate Chemical compound COC(=O)\C=C\C MCVVUJPXSBQTRZ-ONEGZZNKSA-N 0.000 abstract 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
NEW MATERIAL:A 3-(1'-hydroxyethyl)-4-(β,β-disubstituted ethyl)-2-azetidinone shown by the formula II (R1 is alkyl).
EXAMPLE: 3-(1'-Hydroxyethyl)-4-(β,β-dimethoxyethyl)-2-azetidinone.
USE: An intermediate for a novel antibiotic thienamycin [3-(2-aminoethylthio)-6-(1- hydroxyethyl)-7-oxo-1-azabicyclo(3,2,0)hepto-2-ene-2-carboxylic acid]. The use of ?the intermediate can prepare thienamycin industrially advantageously.
PROCESS: A 3-nitropropanaldimethylacetal shown by the formula III is reacted with a methyl crotonate shown by the formula IV (R2 and R3 are lower alkyl) to give an isoxazoline derivative shown by the formula V or VI, which is reduced under moderate pressure to prepare an amine derivative shown by the formula VII. This compound finally undergoes a Grignard reaction to give a compound shown by the formula II.
COPYRIGHT: (C)1981,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8097379A JPS565457A (en) | 1979-06-27 | 1979-06-27 | Thienamycin intermediate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8097379A JPS565457A (en) | 1979-06-27 | 1979-06-27 | Thienamycin intermediate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS565457A true JPS565457A (en) | 1981-01-20 |
Family
ID=13733448
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8097379A Pending JPS565457A (en) | 1979-06-27 | 1979-06-27 | Thienamycin intermediate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS565457A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS567759A (en) * | 1979-07-02 | 1981-01-27 | Dai Ichi Seiyaku Co Ltd | Intermediate of descisdeaminothienamycin |
| JPS5659748A (en) * | 1979-10-20 | 1981-05-23 | Dai Ichi Seiyaku Co Ltd | Intermediate of thienamycin |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5277084A (en) * | 1975-11-21 | 1977-06-29 | Merck & Co Inc | Nn and carboxyl derivatives of thienamycine |
| JPS5334797A (en) * | 1976-09-08 | 1978-03-31 | Smithkline Corp | 77acylaminoo88oxoo33oxaa 11azabicyclo *4*2*0* octanee 22carboxylic acid derivative |
| JPS5466696A (en) * | 1977-10-19 | 1979-05-29 | Merck & Co Inc | 33substitutedd66*1**hydroxyethyl**77oxoo11 azabicyclo*3*2*0**heptoo22enee22carboxylic acid |
-
1979
- 1979-06-27 JP JP8097379A patent/JPS565457A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5277084A (en) * | 1975-11-21 | 1977-06-29 | Merck & Co Inc | Nn and carboxyl derivatives of thienamycine |
| JPS5334797A (en) * | 1976-09-08 | 1978-03-31 | Smithkline Corp | 77acylaminoo88oxoo33oxaa 11azabicyclo *4*2*0* octanee 22carboxylic acid derivative |
| JPS5466696A (en) * | 1977-10-19 | 1979-05-29 | Merck & Co Inc | 33substitutedd66*1**hydroxyethyl**77oxoo11 azabicyclo*3*2*0**heptoo22enee22carboxylic acid |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS567759A (en) * | 1979-07-02 | 1981-01-27 | Dai Ichi Seiyaku Co Ltd | Intermediate of descisdeaminothienamycin |
| JPS5659748A (en) * | 1979-10-20 | 1981-05-23 | Dai Ichi Seiyaku Co Ltd | Intermediate of thienamycin |
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