JPS60233090A - セフエム誘導体の製造方法 - Google Patents

セフエム誘導体の製造方法

Info

Publication number: JPS60233090A
Authority: JP; Japan
Prior art keywords: group; reaction; acid; reactive ester; dimethylformamide
Prior art date: 1984-04-27
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.): Pending

Application number

JP59272168A

Other languages

English (en)

Japanese (ja)

Inventor

金　完柱

李　哲海

金奉鎮

李　寛洵

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.)

KANKOKU KAGAKU GIJIYUTSUIN

KANKOKU KAGAKU GIJUTSUIN

Original Assignee

KANKOKU KAGAKU GIJIYUTSUIN

KANKOKU KAGAKU GIJUTSUIN

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.)

1984-04-27

Filing date

1984-12-25

Publication date

1985-11-19

1984-12-25 Application filed by KANKOKU KAGAKU GIJIYUTSUIN, KANKOKU KAGAKU GIJUTSUIN filed Critical KANKOKU KAGAKU GIJIYUTSUIN

1985-11-19 Publication of JPS60233090A publication Critical patent/JPS60233090A/ja

Status Pending legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims description 7
150000001782 cephems Chemical class 0.000 title claims description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 43
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 30
238000006243 chemical reaction Methods 0.000 claims description 25
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 22
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 22
238000000034 method Methods 0.000 claims description 22
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
150000002148 esters Chemical class 0.000 claims description 15
150000007524 organic acids Chemical class 0.000 claims description 14
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 11
235000017557 sodium bicarbonate Nutrition 0.000 claims description 11
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 11
150000001875 compounds Chemical class 0.000 claims description 10
238000005917 acylation reaction Methods 0.000 claims description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
-1 acetoxymethyl group Chemical group 0.000 claims description 8
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 6
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 6
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 3
239000002585 base Substances 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 3
239000011736 potassium bicarbonate Substances 0.000 claims description 3
235000015497 potassium bicarbonate Nutrition 0.000 claims description 3
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 3
229940086066 potassium hydrogencarbonate Drugs 0.000 claims description 3
229910052783 alkali metal Chemical group 0.000 claims description 2
150000001340 alkali metals Chemical group 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 2
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 claims 2
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 claims 1
235000011114 ammonium hydroxide Nutrition 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
239000000243 solution Substances 0.000 description 23
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
239000000203 mixture Substances 0.000 description 14
239000002244 precipitate Substances 0.000 description 14
238000003756 stirring Methods 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 8
239000003960 organic solvent Substances 0.000 description 7
229920006395 saturated elastomer Polymers 0.000 description 6
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 5
125000006239 protecting group Chemical group 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
239000002253 acid Substances 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
239000013078 crystal Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
239000005973 Carvone Substances 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000005886 esterification reaction Methods 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
235000005985 organic acids Nutrition 0.000 description 3
239000000725 suspension Substances 0.000 description 3
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
239000003782 beta lactam antibiotic agent Substances 0.000 description 2
ULDHMXUKGWMISQ-UHFFFAOYSA-N carvone Chemical compound CC(=C)C1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-UHFFFAOYSA-N 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000047 product Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
239000002132 β-lactam antibiotic Substances 0.000 description 2
229940124586 β-lactam antibiotics Drugs 0.000 description 2
RJFPBECTFIUTHB-INEUFUBQSA-N (6r,7r)-7-azaniumyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound S1CC=C(C(O)=O)N2C(=O)[C@@H](N)[C@H]21 RJFPBECTFIUTHB-INEUFUBQSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 description 1
SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
150000007932 benzotriazole esters Chemical class 0.000 description 1
PPQNDCSTOHZQEH-UHFFFAOYSA-N bis(benzotriazol-1-yl) carbonate Chemical compound N1=NC2=CC=CC=C2N1OC(=O)ON1C2=CC=CC=C2N=N1 PPQNDCSTOHZQEH-UHFFFAOYSA-N 0.000 description 1
JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 description 1
229940047583 cetamide Drugs 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000000498 cooling water Substances 0.000 description 1
HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000032050 esterification Effects 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
210000000936 intestine Anatomy 0.000 description 1
230000007774 longterm Effects 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007858 starting material Substances 0.000 description 1
WEQHQGJDZLDFID-UHFFFAOYSA-J thorium(iv) chloride Chemical compound Cl[Th](Cl)(Cl)Cl WEQHQGJDZLDFID-UHFFFAOYSA-J 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Cephalosporin Compounds (AREA)

JP59272168A 1984-04-27 1984-12-25 セフエム誘導体の製造方法 Pending JPS60233090A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
KR2267/1984		1984-04-27
KR1019840002267A KR850001206B1 (ko)	1984-04-27	1984-04-27	세펨 유도체의 제조 방법

Publications (1)

Publication Number	Publication Date
JPS60233090A true JPS60233090A (ja)	1985-11-19

Family

ID=19233668

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP59272168A Pending JPS60233090A (ja)	1984-04-27	1984-12-25	セフエム誘導体の製造方法

Country Status (6)

Country	Link
JP (1)	JPS60233090A (de)
KR (1)	KR850001206B1 (de)
CH (1)	CH667458A5 (de)
ES (1)	ES540544A0 (de)
GB (1)	GB2158432B (de)
IT (1)	IT1185509B (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
MXPA02006215A (es)	1999-12-22	2003-10-15	Nektar Therapeutics Al Corp	Metodo para preparar esteres de 1-benzotriazolil carbonato de poli(etilenglicol).

Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS591490A (ja) *	1982-06-29	1984-01-06	Dai Ichi Seiyaku Co Ltd	３−セフェム−４−カルボン酸誘導体

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1145744A (fr) *	1979-05-23	1983-05-03	Daniel Farge	Thiovinyl-3 cephalosporines, leur preparation et les compositions qui les contiennent
NL8100089A (nl) *	1980-01-17	1981-08-17	Rhone Poulenc Ind	Nieuwe thiolen en de bereiding daarvan.
US4346076A (en) *	1980-09-17	1982-08-24	Eli Lilly And Company	Bis-tetrazoylmethyl substituted cephalosporin antibiotics

1984
- 1984-04-27 KR KR1019840002267A patent/KR850001206B1/ko not_active Expired
- 1984-09-14 GB GB08423207A patent/GB2158432B/en not_active Expired
- 1984-12-25 JP JP59272168A patent/JPS60233090A/ja active Pending
1985
- 1985-02-18 IT IT19547/85A patent/IT1185509B/it active
- 1985-02-20 ES ES540544A patent/ES540544A0/es active Granted
- 1985-04-16 CH CH1615/85A patent/CH667458A5/de not_active IP Right Cessation

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS591490A (ja) *	1982-06-29	1984-01-06	Dai Ichi Seiyaku Co Ltd	３−セフェム−４−カルボン酸誘導体

Also Published As

Publication number	Publication date
IT8519547A0 (it)	1985-02-18
IT1185509B (it)	1987-11-12
CH667458A5 (de)	1988-10-14
KR850001206B1 (ko)	1985-08-20
GB2158432A (en)	1985-11-13
GB8423207D0 (en)	1984-10-17
GB2158432B (en)	1987-10-28
ES8602018A1 (es)	1985-11-16
ES540544A0 (es)	1985-11-16

Publication	Publication Date	Title
JPH02311483A (ja)	1990-12-27	セフトリアキソンの製造方法
JPH0242085A (ja)	1990-02-13	セフアロスポリン抗生物質の製法
EP0842937A2 (de)	1998-05-20	Verfahren zur Herstellung der Cephalosporinderivate Cefotaxime und Ceftriaxone
JPS60174787A (ja)	1985-09-09	３位置換カルバセフエム化合物
CA2326441C (en)	2008-03-18	Process for purification of a cephalosporin derivative
JPH0553798B2 (de)	1993-08-10
JP2939129B2 (ja)	1999-08-25	セファロスポリンの合成における中間体
JPH0834744B2 (ja)	1996-03-29	新規なセファロスポリン中間体
JPS60233090A (ja)	1985-11-19	セフエム誘導体の製造方法
JP3068143B2 (ja)	2000-07-24	アシル化法
HU200184B (en)	1990-04-28	Process for producing 3-(alkanoyloxymethyl)-3-cefem-4-carboxilic acid derivatie
JPS6254112B2 (de)	1987-11-13
JPS6322585A (ja)	1988-01-30	６−トリフルオロメチル−１ｈ−ベンゾトリアゾ−１−イル−ジフェニルホスフェイト及びセファロスポリン誘導体の製造方法
US4237280A (en)	1980-12-02	Intermediate for cephalosporin type compound
JPH0546354B2 (de)	1993-07-13
JPS62500873A (ja)	1987-04-09	セフアロスポリン誘導体の新規製造方法
US4091214A (en)	1978-05-23	De-esterification process for cephalosporins
KR890004561B1 (ko)	1989-11-15	세펨유도체의 제조방법
JPS63139184A (ja)	1988-06-10	６−〔Ｄ（−）−α−（４−エチル−２，３−ジオキソピペラジン−１−イルカルボニルアミノ）−α−フェニルアセトアミド〕−ペニシラン酸の製法
HU197579B (en)	1989-04-28	Process for production of derivatives of cefem carbonic acid
JPH0161116B2 (de)	1989-12-27
KR0184037B1 (ko)	1999-05-01	세펨 유도체의 제조방법
JPH02138282A (ja)	1990-05-28	セファロスポリン化合物の製造法
JPS5951552B2 (ja)	1984-12-14	ペニシリンヒドラジド誘導体の製造法
JPS60260583A (ja)	1985-12-23	セフアロスポリン誘導体の製法