SE438330B - Forfarande for framstellning av azetidinoner - Google Patents
Forfarande for framstellning av azetidinonerInfo
- Publication number
- SE438330B SE438330B SE7807489A SE7807489A SE438330B SE 438330 B SE438330 B SE 438330B SE 7807489 A SE7807489 A SE 7807489A SE 7807489 A SE7807489 A SE 7807489A SE 438330 B SE438330 B SE 438330B
- Authority
- SE
- Sweden
- Prior art keywords
- formula
- compound
- give
- iii
- azetidinone
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 17
- -1 α-aminobenzyl Chemical group 0.000 claims description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 239000000741 silica gel Substances 0.000 claims description 4
- 229910002027 silica gel Inorganic materials 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 2
- 150000001266 acyl halides Chemical class 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 238000003776 cleavage reaction Methods 0.000 claims description 2
- 238000006073 displacement reaction Methods 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052987 metal hydride Inorganic materials 0.000 claims description 2
- 150000004681 metal hydrides Chemical class 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 230000007017 scission Effects 0.000 claims description 2
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 claims 2
- 230000006181 N-acylation Effects 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 238000005978 reductive desulfurization reaction Methods 0.000 claims 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 150000003952 β-lactams Chemical group 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 1
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
- TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 101100298295 Drosophila melanogaster flfl gene Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 150000001539 azetidines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- FVTCRASFADXXNN-SCRDCRAPSA-N flavin mononucleotide Chemical compound OP(=O)(O)OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O FVTCRASFADXXNN-SCRDCRAPSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- XFZHTGSNSUUBOU-UHFFFAOYSA-N methyl 2-(3-bromo-4-methoxyphenyl)-2-[2-oxo-3-[(2-phenylacetyl)amino]azetidin-1-yl]acetate Chemical compound C=1C=C(OC)C(Br)=CC=1C(C(=O)OC)N(C1=O)CC1NC(=O)CC1=CC=CC=C1 XFZHTGSNSUUBOU-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003548 thiazolidines Chemical class 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- 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
- C07D205/09—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 sulfur atom directly attached in position 4
-
- 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
- C07D205/09—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 sulfur atom directly attached in position 4
- C07D205/095—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 sulfur atom directly attached in position 4 and with a nitrogen atom directly attached in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2819377 | 1977-07-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7807489L SE7807489L (sv) | 1979-01-06 |
| SE438330B true SE438330B (sv) | 1985-04-15 |
Family
ID=10271774
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7807489A SE438330B (sv) | 1977-07-05 | 1978-07-03 | Forfarande for framstellning av azetidinoner |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4230619A (de) |
| JP (1) | JPS5414962A (de) |
| AT (1) | AT359190B (de) |
| AU (1) | AU3766278A (de) |
| BE (1) | BE868710A (de) |
| CA (1) | CA1152085A (de) |
| CH (1) | CH634555A5 (de) |
| DE (1) | DE2829315A1 (de) |
| DK (1) | DK300178A (de) |
| FR (1) | FR2396751A1 (de) |
| GB (1) | GB2017104B (de) |
| IE (1) | IE47063B1 (de) |
| IL (1) | IL55077A0 (de) |
| NL (1) | NL7806860A (de) |
| NO (1) | NO149774C (de) |
| SE (1) | SE438330B (de) |
| ZA (1) | ZA783812B (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GR81665B (de) * | 1983-02-02 | 1984-12-12 | Univ Notre Dame Du Lac | |
| US5106475A (en) * | 1989-09-20 | 1992-04-21 | Eli Lilly And Company | Process for preparing 4-substituted azetidinones |
| US4992545A (en) * | 1989-09-20 | 1991-02-12 | Eli Lilly And Company | Process for preparing 4-substituted azetidinones |
| US6723727B1 (en) * | 1996-12-20 | 2004-04-20 | Hoechst Aktiengesellschaft | Substituted purine derivatives, processes for their preparation, their use, and compositions comprising them |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1368231A (en) * | 1970-07-31 | 1974-09-25 | Glaxo Lab Ltd | Thio-substituted azetidinones and thiazolino azetidinones |
| BE794659A (fr) * | 1972-01-28 | 1973-07-30 | Glaxo Lab Ltd | Procede de preparation de composes intermediaires pour l'obtention d'antibiotiques de type beta-lactame |
| IT1043958B (it) * | 1974-05-22 | 1980-02-29 | Farmaceutici Italia | Procedimento per la preparazione di cefalosporine |
| FR2278335A1 (fr) * | 1974-07-04 | 1976-02-13 | Fujisawa Pharmaceutical Co | Derives d'azetidinones et leurs procedes de preparation |
| BE830934A (fr) * | 1974-07-04 | 1976-01-02 | Derives d'azetidinones et leurs procedes de preparation | |
| FR2335212A2 (fr) * | 1974-07-04 | 1977-07-15 | Fujisawa Pharmaceutical Co | Azetidinones et procede pour leur preparation |
| JPS5175056A (en) * | 1974-12-23 | 1976-06-29 | Fujisawa Pharmaceutical Co | 33 chikanazejinonjudotaino seizoho |
| DE2615621A1 (de) * | 1975-04-10 | 1976-10-21 | Massachusetts Inst Technology | Beta-lactam-antibiotika und -zwischenprodukte sowie ihr herstellungsverfahren |
| GB1570278A (en) * | 1975-10-06 | 1980-06-25 | Fujisawa Pharmaceutical Co | O-substituted-2-azetidinone derivatives and the preparation thereof |
| US4075219A (en) * | 1977-03-31 | 1978-02-21 | Eli Lilly And Company | Epimerization process |
-
1978
- 1978-06-26 NL NL7806860A patent/NL7806860A/xx not_active Application Discontinuation
- 1978-06-30 US US05/921,070 patent/US4230619A/en not_active Expired - Lifetime
- 1978-06-30 IE IE1325/78A patent/IE47063B1/en unknown
- 1978-06-30 AU AU37662/78A patent/AU3766278A/en active Pending
- 1978-06-30 GB GB7914816A patent/GB2017104B/en not_active Expired
- 1978-07-03 AT AT480778A patent/AT359190B/de not_active IP Right Cessation
- 1978-07-03 NO NO782301A patent/NO149774C/no unknown
- 1978-07-03 ZA ZA00783812A patent/ZA783812B/xx unknown
- 1978-07-03 DK DK783001A patent/DK300178A/da not_active Application Discontinuation
- 1978-07-03 SE SE7807489A patent/SE438330B/sv unknown
- 1978-07-04 BE BE189050A patent/BE868710A/xx not_active IP Right Cessation
- 1978-07-04 DE DE19782829315 patent/DE2829315A1/de not_active Withdrawn
- 1978-07-04 IL IL55077A patent/IL55077A0/xx unknown
- 1978-07-04 JP JP8137878A patent/JPS5414962A/ja active Pending
- 1978-07-04 FR FR7819860A patent/FR2396751A1/fr active Granted
- 1978-07-04 CH CH726278A patent/CH634555A5/de not_active IP Right Cessation
- 1978-07-05 CA CA000306800A patent/CA1152085A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IE47063B1 (en) | 1983-12-14 |
| ATA480778A (de) | 1980-03-15 |
| NO782301L (no) | 1979-01-08 |
| IL55077A0 (en) | 1978-09-29 |
| BE868710A (fr) | 1979-01-04 |
| US4230619A (en) | 1980-10-28 |
| DK300178A (da) | 1979-01-06 |
| NO149774B (no) | 1984-03-12 |
| JPS5414962A (en) | 1979-02-03 |
| GB2017104A (en) | 1979-10-03 |
| IE781325L (en) | 1979-01-05 |
| DE2829315A1 (de) | 1979-01-25 |
| GB2017104B (en) | 1982-01-20 |
| SE7807489L (sv) | 1979-01-06 |
| AT359190B (de) | 1980-10-27 |
| NL7806860A (nl) | 1979-01-09 |
| FR2396751B1 (de) | 1983-05-13 |
| CA1152085A (en) | 1983-08-16 |
| ZA783812B (en) | 1979-07-25 |
| AU3766278A (en) | 1980-01-03 |
| NO149774C (no) | 1984-06-20 |
| FR2396751A1 (fr) | 1979-02-02 |
| CH634555A5 (de) | 1983-02-15 |
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