JPS61243079A - １−（アルコキシカルボニルアルキル）−４−（２−フリル）−３−置換−２−アゼチジノン及びその製造方法 - Google Patents
１−（アルコキシカルボニルアルキル）−４−（２−フリル）−３−置換−２−アゼチジノン及びその製造方法Info
- Publication number
- JPS61243079A JPS61243079A JP6866385A JP6866385A JPS61243079A JP S61243079 A JPS61243079 A JP S61243079A JP 6866385 A JP6866385 A JP 6866385A JP 6866385 A JP6866385 A JP 6866385A JP S61243079 A JPS61243079 A JP S61243079A
- Authority
- JP
- Japan
- Prior art keywords
- azetidinone
- chlorine
- formula
- hydrogen
- general formula
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- 239000002262 Schiff base Substances 0.000 claims abstract description 7
- 150000004753 Schiff bases Chemical class 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 claims abstract description 5
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical class CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000460 chlorine Substances 0.000 claims description 19
- 229910052801 chlorine Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- -1 4-(2-furyl)-3-substituted-2-azetidinone Chemical class 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 abstract description 18
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 5
- 150000001412 amines Chemical class 0.000 abstract description 3
- ARLCXYGEMWEXCN-UHFFFAOYSA-N 2-(2-amino-1,3-thiazol-4-yl)-2-methoxyimino-n-(2-oxoazetidin-3-yl)acetamide Chemical class C=1SC(N)=NC=1C(=NOC)C(=O)NC1CNC1=O ARLCXYGEMWEXCN-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 150000003973 alkyl amines Chemical class 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical class O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LBHATBBOPIGUKB-UHFFFAOYSA-N 2-azidoethenone Chemical compound [N-]=[N+]=NC=C=O LBHATBBOPIGUKB-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 244000309464 bull Species 0.000 description 3
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 description 2
- 101150041968 CDC13 gene Proteins 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000006352 cycloaddition reaction Methods 0.000 description 2
- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- FONOSWYYBCBQGN-UHFFFAOYSA-N ethylene dione Chemical class O=C=C=O FONOSWYYBCBQGN-UHFFFAOYSA-N 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- UVEWQKMPXAHFST-UHFFFAOYSA-N n,1-diphenylmethanimine Chemical class C=1C=CC=CC=1C=NC1=CC=CC=C1 UVEWQKMPXAHFST-UHFFFAOYSA-N 0.000 description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
- FRYULBDUGHHPIU-UHFFFAOYSA-N 2-(4-nitrophenyl)ethenone Chemical compound [O-][N+](=O)C1=CC=C(C=C=O)C=C1 FRYULBDUGHHPIU-UHFFFAOYSA-N 0.000 description 1
- SUHXTVABLHHRST-UHFFFAOYSA-N 2-azidoacetyl chloride Chemical compound ClC(=O)CN=[N+]=[N-] SUHXTVABLHHRST-UHFFFAOYSA-N 0.000 description 1
- MIFXURDBXVFMHR-UHFFFAOYSA-N 2-methoxyethenone Chemical class COC=C=O MIFXURDBXVFMHR-UHFFFAOYSA-N 0.000 description 1
- VDOKWPVSGXHSNP-UHFFFAOYSA-N 2-methylprop-1-en-1-one Chemical compound CC(C)=C=O VDOKWPVSGXHSNP-UHFFFAOYSA-N 0.000 description 1
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 150000001804 chlorine Chemical group 0.000 description 1
- OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- ZWJPCOALBPMBIC-UHFFFAOYSA-N diphenylketene Chemical compound C=1C=CC=CC=1C(=C=O)C1=CC=CC=C1 ZWJPCOALBPMBIC-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- DRDBNKYFCOLNQO-UHFFFAOYSA-N ethyl n-phenylmethanimidate Chemical compound CCOC=NC1=CC=CC=C1 DRDBNKYFCOLNQO-UHFFFAOYSA-N 0.000 description 1
- 150000002561 ketenes Chemical class 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000006303 photolysis reaction Methods 0.000 description 1
- 230000015843 photosynthesis, light reaction Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6866385A JPS61243079A (ja) | 1985-04-01 | 1985-04-01 | １−（アルコキシカルボニルアルキル）−４−（２−フリル）−３−置換−２−アゼチジノン及びその製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6866385A JPS61243079A (ja) | 1985-04-01 | 1985-04-01 | １−（アルコキシカルボニルアルキル）−４−（２−フリル）−３−置換−２−アゼチジノン及びその製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61243079A true JPS61243079A (ja) | 1986-10-29 |
| JPH0451555B2 JPH0451555B2 (enrdf_load_stackoverflow) | 1992-08-19 |
Family
ID=13380173
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6866385A Granted JPS61243079A (ja) | 1985-04-01 | 1985-04-01 | １−（アルコキシカルボニルアルキル）−４−（２−フリル）−３−置換−２−アゼチジノン及びその製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61243079A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4940520A (en) * | 1989-06-21 | 1990-07-10 | Merck & Co., Inc. | Process for the preparation of 4-acyloxyazetidin-2-one by singlet oxygen oxidation |
| US4952288A (en) * | 1989-06-21 | 1990-08-28 | Merck & Co., Inc. | Process for the preparation of 4-acyloxyazetidin-2-one by electrochemical methods |
| EP1227093A3 (en) * | 1993-03-22 | 2002-08-07 | Florida State University | Beta-lactams useful for preparation of taxanes having furyl or thienyl substituted side-chain |
-
1985
- 1985-04-01 JP JP6866385A patent/JPS61243079A/ja active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4940520A (en) * | 1989-06-21 | 1990-07-10 | Merck & Co., Inc. | Process for the preparation of 4-acyloxyazetidin-2-one by singlet oxygen oxidation |
| US4952288A (en) * | 1989-06-21 | 1990-08-28 | Merck & Co., Inc. | Process for the preparation of 4-acyloxyazetidin-2-one by electrochemical methods |
| EP1227093A3 (en) * | 1993-03-22 | 2002-08-07 | Florida State University | Beta-lactams useful for preparation of taxanes having furyl or thienyl substituted side-chain |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0451555B2 (enrdf_load_stackoverflow) | 1992-08-19 |
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