JPS5553286A - Preparation of azetidine derivative - Google Patents
Preparation of azetidine derivativeInfo
- Publication number
- JPS5553286A JPS5553286A JP12645178A JP12645178A JPS5553286A JP S5553286 A JPS5553286 A JP S5553286A JP 12645178 A JP12645178 A JP 12645178A JP 12645178 A JP12645178 A JP 12645178A JP S5553286 A JPS5553286 A JP S5553286A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- chloramine
- acid
- penicillin derivative
- reacting
- 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
- 150000001539 azetidines Chemical class 0.000 title 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- VDQQXEISLMTGAB-UHFFFAOYSA-N chloramine T Chemical compound [Na+].CC1=CC=C(S(=O)(=O)[N-]Cl)C=C1 VDQQXEISLMTGAB-UHFFFAOYSA-N 0.000 abstract 2
- 150000002960 penicillins Chemical class 0.000 abstract 2
- 229960001479 tosylchloramide sodium Drugs 0.000 abstract 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical group N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 238000000354 decomposition reaction Methods 0.000 abstract 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- CHVZPRDGLWBEMJ-UHFFFAOYSA-N n-chlorobenzenesulfonamide Chemical compound ClNS(=O)(=O)C1=CC=CC=C1 CHVZPRDGLWBEMJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
Abstract
PURPOSE: To prepare the title compound useful as an synthetic intermediate of antibiotic substance, easily, by reacting a penicillin derivative with a compound such as chloramine-T which is safe, easily handleable, and low-cost compound, and an acid, in the presence of a lower alcohol, at a specific pH range.
CONSTITUTION: A compound III is prepared by reacting a penicillin derivative I [R1 is (substituted) alkyl, aryl, or arylalkyl] with a compound II (R is lower alkyl; n is 0W3; M is alkali metal; X is halogen), e.g. chloramine-T, chloramine-B or chloramine-X, and an acid, e.g. acetic acid, in the presence of a lower alcohol of formula R2-OH (R2 is lower alkyl),e.g. methanol, at pH3W8, in an inert organic solvent such as acetone. To prevent the decomposition of the penicillin derivative and to proceed the reaction, it is necessary to keep the pH of the reaction system between 3 and 8 by adding the compound II and the acid gradually and alterately to the reaction system.
COPYRIGHT: (C)1980,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12645178A JPS5553286A (en) | 1978-10-14 | 1978-10-14 | Preparation of azetidine derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12645178A JPS5553286A (en) | 1978-10-14 | 1978-10-14 | Preparation of azetidine derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS5553286A true JPS5553286A (en) | 1980-04-18 |
Family
ID=14935533
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12645178A Pending JPS5553286A (en) | 1978-10-14 | 1978-10-14 | Preparation of azetidine derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5553286A (en) |
-
1978
- 1978-10-14 JP JP12645178A patent/JPS5553286A/en active Pending
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