JPS5799589A - Penicillin derivative and its preparation - Google Patents
Penicillin derivative and its preparationInfo
- Publication number
- JPS5799589A JPS5799589A JP55176303A JP17630380A JPS5799589A JP S5799589 A JPS5799589 A JP S5799589A JP 55176303 A JP55176303 A JP 55176303A JP 17630380 A JP17630380 A JP 17630380A JP S5799589 A JPS5799589 A JP S5799589A
- Authority
- JP
- Japan
- Prior art keywords
- formulai
- alkylthio
- penicillin derivative
- preparation
- compound
- 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
- 150000002960 penicillins Chemical class 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 125000004414 alkyl thio group Chemical group 0.000 abstract 2
- 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 abstract 1
- WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 abstract 1
- 125000005110 aryl thio group Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000011261 inert gas Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 238000007086 side reaction Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
Classifications
-
- 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
Abstract
NEW MATERIAL:A penicillin derivative shown by the formulaI(Y is Br, alkylthio, arylthio, etc.; R is H, carboxy-protecting group; n is 0W2; with the proviso that when n=0, Y is not Br).
EXAMPLE: Methyl 6 α-bromo-6β-[(R)-1'-hydroxyethyl]-β-oxopenicillanate shown by the formula II.
USE: An intermediate for synthesizing a simulant compound of thienamycin.
PROCESS: A compound shown by the formula III (X and Y are Br and n is 1 or 2; X=H, Y is alkylthio, etc. or X and Y are alkylseleno and n=0) is treated with an alkyllithium or alkylmagnesium, and reacted with acetaldehyde to give the desired compound shown by the formulaI. The reaction is preferably carried out in a solvent (e.g., THF) at low temperature -78W-20°C under an inert gas (e.g., nitrogen) flow to suppress side reactions.
COPYRIGHT: (C)1982,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55176303A JPS5799589A (en) | 1980-12-13 | 1980-12-13 | Penicillin derivative and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55176303A JPS5799589A (en) | 1980-12-13 | 1980-12-13 | Penicillin derivative and its preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS5799589A true JPS5799589A (en) | 1982-06-21 |
Family
ID=16011222
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP55176303A Pending JPS5799589A (en) | 1980-12-13 | 1980-12-13 | Penicillin derivative and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5799589A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010095617A1 (en) * | 2009-02-19 | 2010-08-26 | 大塚化学株式会社 | Process for producing 4-chloroazetidinone compound |
-
1980
- 1980-12-13 JP JP55176303A patent/JPS5799589A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010095617A1 (en) * | 2009-02-19 | 2010-08-26 | 大塚化学株式会社 | Process for producing 4-chloroazetidinone compound |
| JP5791498B2 (en) * | 2009-02-19 | 2015-10-07 | 大塚化学株式会社 | Process for producing 4-chloroazetidinone compound |
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