IL42148A - Process for preparing desacetoxycephalosporins from penicillin sulfoxides and new silyl esters of azetidine-2-sulfenates - Google Patents
Process for preparing desacetoxycephalosporins from penicillin sulfoxides and new silyl esters of azetidine-2-sulfenatesInfo
- Publication number
- IL42148A IL42148A IL42148A IL4214873A IL42148A IL 42148 A IL42148 A IL 42148A IL 42148 A IL42148 A IL 42148A IL 4214873 A IL4214873 A IL 4214873A IL 42148 A IL42148 A IL 42148A
- Authority
- IL
- Israel
- Prior art keywords
- hydrogen
- alkyl
- compound
- trimethylsilyl
- phenyl
- Prior art date
Links
- -1 penicillin sulfoxides Chemical class 0.000 title claims 20
- BRADTAJXVOECJE-UHFFFAOYSA-N 2-hydroxysulfanylazetidine Chemical class OSC1CCN1 BRADTAJXVOECJE-UHFFFAOYSA-N 0.000 title claims 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 title claims 2
- 229930182555 Penicillin Natural products 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 229940049954 penicillin Drugs 0.000 title 1
- 238000000034 method Methods 0.000 claims 15
- 239000001257 hydrogen Substances 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 230000002378 acidificating effect Effects 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 6
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 239000003795 chemical substances by application Substances 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 4
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims 4
- FCZNNHHXCFARDY-WQRUCBPWSA-N (2s,5r,6r)-3,3-dimethyl-4,7-dioxo-6-[(2-phenylacetyl)amino]-4$l^{4}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound N([C@H]1[C@@H]2N(C1=O)[C@H](C(S2=O)(C)C)C(O)=O)C(=O)CC1=CC=CC=C1 FCZNNHHXCFARDY-WQRUCBPWSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 125000005544 phthalimido group Chemical group 0.000 claims 3
- 150000003254 radicals Chemical class 0.000 claims 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 2
- 125000004423 acyloxy group Chemical group 0.000 claims 2
- 125000001589 carboacyl group Chemical group 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 150000002431 hydrogen Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 150000002642 lithium compounds Chemical class 0.000 claims 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- LWFWUJCJKPUZLV-UHFFFAOYSA-N n-trimethylsilylacetamide Chemical compound CC(=O)N[Si](C)(C)C LWFWUJCJKPUZLV-UHFFFAOYSA-N 0.000 claims 2
- 125000006502 nitrobenzyl group Chemical group 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- 239000005051 trimethylchlorosilane Substances 0.000 claims 2
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- GVHIREZHTRULPT-UHFFFAOYSA-N 2-methyl-n-trimethylsilylpropan-2-amine Chemical compound CC(C)(C)N[Si](C)(C)C GVHIREZHTRULPT-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 claims 1
- XCOBLONWWXQEBS-KPKJPENVSA-N N,O-bis(trimethylsilyl)trifluoroacetamide Chemical compound C[Si](C)(C)O\C(C(F)(F)F)=N\[Si](C)(C)C XCOBLONWWXQEBS-KPKJPENVSA-N 0.000 claims 1
- JOOMLFKONHCLCJ-UHFFFAOYSA-N N-(trimethylsilyl)diethylamine Chemical compound CCN(CC)[Si](C)(C)C JOOMLFKONHCLCJ-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000005042 acyloxymethyl group Chemical group 0.000 claims 1
- 125000003302 alkenyloxy group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 1
- RLECCBFNWDXKPK-UHFFFAOYSA-N bis(trimethylsilyl)sulfide Chemical compound C[Si](C)(C)S[Si](C)(C)C RLECCBFNWDXKPK-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Chemical group 0.000 claims 1
- QABCGOSYZHCPGN-UHFFFAOYSA-N chloro(dimethyl)silicon Chemical compound C[Si](C)Cl QABCGOSYZHCPGN-UHFFFAOYSA-N 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 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
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000005179 haloacetyl group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 claims 1
- 229940073561 hexamethyldisiloxane Drugs 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 claims 1
- 229910003002 lithium salt Inorganic materials 0.000 claims 1
- 159000000002 lithium salts Chemical class 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- QHUOBLDKFGCVCG-UHFFFAOYSA-N n-methyl-n-trimethylsilylacetamide Chemical compound CC(=O)N(C)[Si](C)(C)C QHUOBLDKFGCVCG-UHFFFAOYSA-N 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000006501 nitrophenyl group Chemical group 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 229910052717 sulfur Chemical group 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- YKPHTSHERCDMCL-UHFFFAOYSA-N trimethyl(prop-1-enoxy)silane Chemical compound CC=CO[Si](C)(C)C YKPHTSHERCDMCL-UHFFFAOYSA-N 0.000 claims 1
- NTJPIRDYMVYFNP-UHFFFAOYSA-M trimethylsilylmethanesulfonate Chemical compound C[Si](C)(C)CS([O-])(=O)=O NTJPIRDYMVYFNP-UHFFFAOYSA-M 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25207872A | 1972-05-10 | 1972-05-10 | |
| US05/349,876 US3944545A (en) | 1972-05-10 | 1973-04-12 | Process for preparing desacetoxycephalosporins |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL42148A0 IL42148A0 (en) | 1973-06-29 |
| IL42148A true IL42148A (en) | 1976-08-31 |
Family
ID=26942026
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL42148A IL42148A (en) | 1972-05-10 | 1973-04-30 | Process for preparing desacetoxycephalosporins from penicillin sulfoxides and new silyl esters of azetidine-2-sulfenates |
Country Status (21)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA732972B (en) * | 1972-05-10 | 1974-11-27 | Lilly Co Eli | Process for preparing desacetoxycephalosporins and novel intermediates |
| GB1465893A (en) * | 1973-02-09 | 1977-03-02 | Gist Brocades Nv | I-carboxypropenyl-4-iminothio-azetidine-2-one derivatives methods for their preparation and use |
| US4159266A (en) * | 1974-12-24 | 1979-06-26 | Eli Lilly And Company | Method of preparation of 3-methylenecephams |
| AT342197B (de) * | 1975-02-20 | 1978-03-28 | Ciba Geigy Ag | Neues verfahren zur herstellung von 3-cephemverbindungen |
| JPS5214789A (en) * | 1975-07-22 | 1977-02-03 | Shionogi & Co Ltd | Process for preparing 3-substiuted cephem compounds by ring closure |
| US4536334A (en) * | 1979-06-28 | 1985-08-20 | Sumitomo Chemical Company, Limited | Preparation of β-lactam derivatives |
| US5302713A (en) * | 1992-03-31 | 1994-04-12 | Industrial Technology Research Institute | Method for the preparation of Δ3 -7-substituted amino desacetoxy cephalosporanic acid |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3591585A (en) * | 1969-02-14 | 1971-07-06 | Lilly Co Eli | Process for making desacetoxycephalosporins |
| US3819622A (en) * | 1969-03-11 | 1974-06-25 | Glaxo Lab Ltd | Method of producing 7beta-acylamido-3-methylceph-3-em-4-carboxylic acid esters |
| FR2037858A5 (US07696358-20100413-C00002.png) * | 1969-03-11 | 1970-12-31 | Glaxo Lab Ltd | |
| GB1312233A (en) * | 1969-12-05 | 1973-04-04 | Glaxo Lab Ltd | Cephalosporin compounds |
-
1973
- 1973-04-12 US US05/349,876 patent/US3944545A/en not_active Expired - Lifetime
- 1973-04-30 GB GB2034873A patent/GB1412856A/en not_active Expired
- 1973-04-30 IL IL42148A patent/IL42148A/en unknown
- 1973-05-03 CA CA170,357A patent/CA1026744A/en not_active Expired
- 1973-05-03 AU AU55197/73A patent/AU476568B2/en not_active Expired
- 1973-05-07 IE IE717/73A patent/IE38150B1/xx unknown
- 1973-05-08 HU HUEI561A patent/HU170406B/hu unknown
- 1973-05-08 HU HUEI475A patent/HU166698B/hu unknown
- 1973-05-09 CH CH654773A patent/CH582187A5/xx not_active IP Right Cessation
- 1973-05-09 AT AT410573A patent/AT333424B/de not_active IP Right Cessation
- 1973-05-09 SE SE7306497A patent/SE429046B/xx unknown
- 1973-05-09 NL NL7306500A patent/NL7306500A/xx not_active Application Discontinuation
- 1973-05-09 DE DE2323395A patent/DE2323395A1/de not_active Withdrawn
- 1973-05-09 YU YU1219/73A patent/YU36925B/xx unknown
- 1973-05-10 DD DD180331*A patent/DD116617A5/xx unknown
- 1973-05-10 BG BG023570A patent/BG20816A3/xx unknown
- 1973-05-10 JP JP5204773A patent/JPS5418276B2/ja not_active Expired
- 1973-05-10 DD DD170755A patent/DD108302A5/xx unknown
- 1973-05-10 PH PH14603A patent/PH14066A/en unknown
- 1973-05-10 CS CS733319A patent/CS197217B2/cs unknown
- 1973-05-10 AR AR247948A patent/AR203722A1/es active
- 1973-05-10 FR FR7316915A patent/FR2184069B1/fr not_active Expired
- 1973-05-10 ES ES414645A patent/ES414645A1/es not_active Expired
- 1973-05-10 BG BG027289A patent/BG20380A3/xx unknown
-
1976
- 1976-03-29 CH CH654773A patent/CH580638A5/xx not_active IP Right Cessation
- 1976-04-15 SE SE7604463A patent/SE429968B/xx not_active IP Right Cessation
-
1978
- 1978-07-28 JP JP53092451A patent/JPS585917B2/ja not_active Expired
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