JPS6219432B2 - - Google Patents

Info

Publication number: JPS6219432B2
Authority: JP; Japan
Prior art keywords: formula; methyl; carboxylic acid; compound represented; mmol
Prior art date: 1979-12-25
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.): Expired

Application number

JP54167671A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5690089A (en

Inventor

Yasuo Hoshiide

Yoshio Hashimoto

Kenichi Suzuki

Takeji Seki

Naryuki Tasaka

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Nikken Chemicals Co Ltd

Original Assignee

Nikken Chemicals Co Ltd

Priority date (The priority date 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 date listed.)

1979-12-25

Filing date

1979-12-25

Publication date

1987-04-28

1979-12-25 Application filed by Nikken Chemicals Co Ltd filed Critical Nikken Chemicals Co Ltd

1979-12-25 Priority to JP16767179A priority Critical patent/JPS5690089A/ja

1981-07-21 Publication of JPS5690089A publication Critical patent/JPS5690089A/ja

1987-04-28 Publication of JPS6219432B2 publication Critical patent/JPS6219432B2/ja

Status Granted legal-status Critical Current

Links

OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 45
-1 7-methoxycephem compound Chemical class 0.000 claims description 34
150000001875 compounds Chemical class 0.000 claims description 18
238000000034 method Methods 0.000 claims description 14
125000000217 alkyl group Chemical group 0.000 claims description 9
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 9
239000004327 boric acid Substances 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 5
125000006244 carboxylic acid protecting group Chemical group 0.000 claims description 4
230000002194 synthesizing effect Effects 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 10
238000004519 manufacturing process Methods 0.000 description 8
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
150000003952 β-lactams Chemical class 0.000 description 8
239000002904 solvent Substances 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
238000004440 column chromatography Methods 0.000 description 6
239000013078 crystal Substances 0.000 description 6
VDQQXEISLMTGAB-UHFFFAOYSA-N chloramine T Chemical compound [Na+].CC1=CC=C(S(=O)(=O)[N-]Cl)C=C1 VDQQXEISLMTGAB-UHFFFAOYSA-N 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
239000013076 target substance Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 description 2
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
GYQRIAVRKLRQKP-UHFFFAOYSA-N methyl 2-chloro-3-oxobutanoate Chemical compound COC(=O)C(Cl)C(C)=O GYQRIAVRKLRQKP-UHFFFAOYSA-N 0.000 description 2
NDTWZHURUDSPQV-UHFFFAOYSA-N methyl 2-methyl-3-oxobutanoate Chemical compound COC(=O)C(C)C(C)=O NDTWZHURUDSPQV-UHFFFAOYSA-N 0.000 description 2
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
YEVAUDUCLFERSB-ULUSZKPHSA-N (6r)-4-methoxy-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical class C1=CC(OC)S[C@@H]2CC(=O)N21 YEVAUDUCLFERSB-ULUSZKPHSA-N 0.000 description 1
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
MIDXCONKKJTLDX-UHFFFAOYSA-N 3,5-dimethylcyclopentane-1,2-dione Chemical group CC1CC(C)C(=O)C1=O MIDXCONKKJTLDX-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
108090000204 Dipeptidase 1 Proteins 0.000 description 1
101000933374 Gallus gallus Brain-specific homeobox/POU domain protein 3 Proteins 0.000 description 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 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
239000002585 base Substances 0.000 description 1
UAZSJWADJKHHSJ-CYBMUJFWSA-N benzyl (6R)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C(C1=CC=CC=C1)OC(=O)C1=CCS[C@H]2N1C(C2)=O UAZSJWADJKHHSJ-CYBMUJFWSA-N 0.000 description 1
102000006635 beta-lactamase Human genes 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
KFCUPNHUPHDVJC-UHFFFAOYSA-N bromine azide Chemical compound BrN=[N+]=[N-] KFCUPNHUPHDVJC-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
238000006198 methoxylation reaction Methods 0.000 description 1
YXLVLOWNJCOOAU-UHFFFAOYSA-N methyl 2-ethyl-3-oxobutanoate Chemical compound CCC(C(C)=O)C(=O)OC YXLVLOWNJCOOAU-UHFFFAOYSA-N 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000000047 product Substances 0.000 description 1
239000002994 raw material Substances 0.000 description 1
229910001923 silver oxide Inorganic materials 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1

Classifications

- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Cephalosporin Compounds (AREA)

JP16767179A 1979-12-25 1979-12-25 Synthesis of 7-methoxycephem compound Granted JPS5690089A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP16767179A JPS5690089A (en)	1979-12-25	1979-12-25	Synthesis of 7-methoxycephem compound

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP16767179A JPS5690089A (en)	1979-12-25	1979-12-25	Synthesis of 7-methoxycephem compound

Publications (2)

Publication Number	Publication Date
JPS5690089A JPS5690089A (en)	1981-07-21
JPS6219432B2 true JPS6219432B2 (fi)	1987-04-28

Family

ID=15854053

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP16767179A Granted JPS5690089A (en)	1979-12-25	1979-12-25	Synthesis of 7-methoxycephem compound

Country Status (1)

Country	Link
JP (1)	JPS5690089A (fi)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5552542A (en) *	1995-05-10	1996-09-03	Bristol-Myers Squibb Company	Preparation and use of 7-[(2-carboalkoxy-1-methylethenyl)amino]-3-hydroxymethyl-3-cephem-4-carboxylic acids

1979
- 1979-12-25 JP JP16767179A patent/JPS5690089A/ja active Granted

Also Published As

Publication number	Publication date
JPS5690089A (en)	1981-07-21

Publication	Publication Date	Title
US4699980A (en)	1987-10-13	Process for preparing 3-substituted-methyl-3-cephem derivatives
JP3713282B2 (ja)	2005-11-09	３−（２−置換−ビニル）−セファロスポリンのｚ異性体の選択的製造方法
JP2731853B2 (ja)	1998-03-25	トリ低級アルカノイルオキシホウ素の製造法
JPS6219432B2 (fi)	1987-04-28
EP0015629B1 (en)	1986-01-02	New intermediates for the preparation of cephalosporins and process for the preparation of the intermediates
EP0117872B1 (en)	1991-08-21	Process for preparing cephalosporin compounds
US4118563A (en)	1978-10-03	Production of 7-(2-aminomethylphenylacetamido-3-(1-carboxymethyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid
KR890002107B1 (ko)	1989-06-19	세팔로스포린 유도체의 제조방법
KR910005230B1 (ko)	1991-07-24	아제티디논의 제조방법
JPS6219431B2 (fi)	1987-04-28
EP0096496B1 (en)	1986-07-23	Preparation of penicillin and cephalosporin compounds and novel intermediates useful therein
EP0308123B1 (en)	1993-12-08	Crystalline antibiotic intermediate
JPH0358351B2 (fi)	1991-09-05
JPH0354110B2 (fi)	1991-08-19
US4640798A (en)	1987-02-03	Intermediates for the preparation of penicillin and cephalosporin compounds
EP0120094B1 (en)	1989-04-19	Azetidinone compounds
US4006139A (en)	1977-02-01	1,2,4-Dithiaaz-3-enes
KR810000859B1 (ko)	1981-08-10	7-아미노-△³-데스 아세톡시세팔로스포란산 유도체의 제조방법
KR890001284B1 (ko)	1989-04-28	새로운 아실화방법에 의한 세팔로스포린 유도체의 제조방법
JPH0561355B2 (fi)	1993-09-06
KR850001960B1 (ko)	1985-12-31	세팔로스포린 유도체의 제조방법
KR100229175B1 (ko)	1999-11-01	세펨 유도체의 제조방법
KR840002142B1 (ko)	1984-11-23	7α-메톡시세팔로스포린 유도체의 제조방법
JPH0517229B2 (fi)	1993-03-08
JPS6210994B2 (fi)	1987-03-10