SU703023A3 - Способ получени 3-ацилоксиметил- цефемов - Google Patents
Способ получени 3-ацилоксиметил- цефемовInfo
- Publication number
- SU703023A3 SU703023A3 SU772439832A SU2439832A SU703023A3 SU 703023 A3 SU703023 A3 SU 703023A3 SU 772439832 A SU772439832 A SU 772439832A SU 2439832 A SU2439832 A SU 2439832A SU 703023 A3 SU703023 A3 SU 703023A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- carboxylate
- nitrobenzyl
- methylene
- mixture
- added
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 19
- 239000000203 mixture Substances 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- -1 p-nitrobenzyloxy, phenoxymethyl Chemical group 0.000 description 6
- 150000003462 sulfoxides Chemical class 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- UEWXBFLOCSAEKP-UBVWURDFSA-N (4-nitrophenyl)methyl (6r)-3-(acetyloxymethyl)-8-oxo-7-[(2-phenoxyacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylate Chemical compound C1([C@H]2SC=C(C(N2C1=O)C(=O)OCC=1C=CC(=CC=1)[N+]([O-])=O)COC(=O)C)NC(=O)COC1=CC=CC=C1 UEWXBFLOCSAEKP-UBVWURDFSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 229930182555 Penicillin Natural products 0.000 description 3
- 239000012346 acetyl chloride Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 125000006502 nitrobenzyl group Chemical group 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 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 description 1
- SXBDXXFTJVHSAF-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]oct-3-en-8-one Chemical compound S1C=CCN2C(=O)C[C@H]21 SXBDXXFTJVHSAF-ZCFIWIBFSA-N 0.000 description 1
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
- JYJIMEQNTHFXMT-UHFFFAOYSA-N 2-nitro-2-phenylacetic acid Chemical compound OC(=O)C([N+]([O-])=O)C1=CC=CC=C1 JYJIMEQNTHFXMT-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound 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 description 1
- XVRVTQGFVVJAKK-UHFFFAOYSA-N S(=O)(=O)(Cl)Cl.N1CCC1 Chemical compound S(=O)(=O)(Cl)Cl.N1CCC1 XVRVTQGFVVJAKK-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000003855 acyl compounds Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000006000 trichloroethyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/02—Preparation
- C07D501/04—Preparation from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/650,585 US4031082A (en) | 1976-01-19 | 1976-01-19 | Process for preparing 3-acycloxymethyl-2-cephem compounds |
| US05/650,583 US4029651A (en) | 1976-01-19 | 1976-01-19 | Process for preparing 3-acyloxymethyl-2-cephem compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU703023A3 true SU703023A3 (ru) | 1979-12-05 |
Family
ID=27095900
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU772439832A SU703023A3 (ru) | 1976-01-19 | 1977-01-18 | Способ получени 3-ацилоксиметил- цефемов |
Country Status (25)
| Country | Link |
|---|---|
| JP (1) | JPS5289698A (enExample) |
| AR (1) | AR213426A1 (enExample) |
| AT (1) | AT348121B (enExample) |
| AU (1) | AU503930B2 (enExample) |
| BG (1) | BG30473A3 (enExample) |
| CH (1) | CH628059A5 (enExample) |
| CS (1) | CS192474B2 (enExample) |
| DD (1) | DD128734A5 (enExample) |
| DE (1) | DE2656144C2 (enExample) |
| DK (1) | DK17977A (enExample) |
| FR (1) | FR2338280A1 (enExample) |
| GB (1) | GB1566526A (enExample) |
| GR (1) | GR65892B (enExample) |
| HU (1) | HU173592B (enExample) |
| IE (1) | IE44133B1 (enExample) |
| IL (1) | IL51021A (enExample) |
| MX (1) | MX3766E (enExample) |
| NL (1) | NL7700500A (enExample) |
| NZ (1) | NZ182737A (enExample) |
| PL (1) | PL104370B1 (enExample) |
| PT (1) | PT66007B (enExample) |
| RO (1) | RO69710A (enExample) |
| SE (1) | SE433849B (enExample) |
| SU (1) | SU703023A3 (enExample) |
| YU (1) | YU8677A (enExample) |
-
1976
- 1976-11-26 NZ NZ182737A patent/NZ182737A/xx unknown
- 1976-11-26 GR GR52271A patent/GR65892B/el unknown
- 1976-11-26 IE IE2598/76A patent/IE44133B1/en unknown
- 1976-11-28 IL IL51021A patent/IL51021A/xx unknown
- 1976-12-03 AU AU20238/76A patent/AU503930B2/en not_active Expired
- 1976-12-10 DE DE2656144A patent/DE2656144C2/de not_active Expired
- 1976-12-22 BG BG034974A patent/BG30473A3/xx unknown
- 1976-12-23 PT PT66007A patent/PT66007B/pt unknown
-
1977
- 1977-01-04 SE SE7700077A patent/SE433849B/xx not_active IP Right Cessation
- 1977-01-10 CH CH24877A patent/CH628059A5/de not_active IP Right Cessation
- 1977-01-10 MX MX775319U patent/MX3766E/es unknown
- 1977-01-12 FR FR7700763A patent/FR2338280A1/fr active Granted
- 1977-01-12 JP JP229877A patent/JPS5289698A/ja active Granted
- 1977-01-13 YU YU00086/77A patent/YU8677A/xx unknown
- 1977-01-13 RO RO7789041A patent/RO69710A/ro unknown
- 1977-01-14 GB GB1450/77A patent/GB1566526A/en not_active Expired
- 1977-01-18 DK DK17977A patent/DK17977A/da not_active Application Discontinuation
- 1977-01-18 NL NL7700500A patent/NL7700500A/xx not_active Application Discontinuation
- 1977-01-18 SU SU772439832A patent/SU703023A3/ru active
- 1977-01-18 PL PL1977195386A patent/PL104370B1/pl not_active IP Right Cessation
- 1977-01-18 HU HU77EI723A patent/HU173592B/hu unknown
- 1977-01-19 CS CS77368A patent/CS192474B2/cs unknown
- 1977-01-19 DD DD7700197001A patent/DD128734A5/xx unknown
- 1977-01-19 AT AT28177A patent/AT348121B/de not_active IP Right Cessation
- 1977-01-19 AR AR266243A patent/AR213426A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| RO69710A (ro) | 1980-07-15 |
| IL51021A0 (en) | 1977-01-31 |
| DD128734A5 (de) | 1977-12-07 |
| BG30473A3 (en) | 1981-06-15 |
| PL195386A1 (pl) | 1978-02-27 |
| ATA28177A (de) | 1978-06-15 |
| NL7700500A (nl) | 1977-07-21 |
| CS192474B2 (en) | 1979-08-31 |
| FR2338280A1 (fr) | 1977-08-12 |
| NZ182737A (en) | 1978-04-28 |
| IE44133L (en) | 1977-07-19 |
| SE433849B (sv) | 1984-06-18 |
| HU173592B (hu) | 1979-06-28 |
| PT66007A (en) | 1977-01-01 |
| AR213426A1 (es) | 1979-01-31 |
| PT66007B (en) | 1978-06-16 |
| AT348121B (de) | 1979-01-25 |
| GR65892B (enExample) | 1980-12-01 |
| DK17977A (da) | 1977-07-20 |
| YU8677A (en) | 1982-06-30 |
| PL104370B1 (pl) | 1979-08-31 |
| JPS6120557B2 (enExample) | 1986-05-22 |
| AU2023876A (en) | 1978-06-08 |
| SE7700077L (sv) | 1977-07-20 |
| IE44133B1 (en) | 1981-08-26 |
| IL51021A (en) | 1979-09-30 |
| DE2656144C2 (de) | 1985-08-29 |
| CH628059A5 (en) | 1982-02-15 |
| DE2656144A1 (de) | 1977-07-21 |
| FR2338280B1 (enExample) | 1979-09-28 |
| MX3766E (es) | 1981-06-25 |
| AU503930B2 (en) | 1979-09-27 |
| GB1566526A (en) | 1980-04-30 |
| JPS5289698A (en) | 1977-07-27 |
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