JPS6332062B2 - - Google Patents

Info

Publication number: JPS6332062B2
Authority: JP; Japan
Prior art keywords: acid; ester; reaction; producing; solution
Prior art date: 1980-10-21
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

JP14634380A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5770847A (en

Inventor

Masaji Oono

Hamao Umezawa

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.)

Microbial Chemistry Research Foundation

Original Assignee

Microbial Chemistry Research Foundation

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.)

1980-10-21

Filing date

1980-10-21

Publication date

1988-06-28

1980-10-21 Application filed by Microbial Chemistry Research Foundation filed Critical Microbial Chemistry Research Foundation

1980-10-21 Priority to JP14634380A priority Critical patent/JPS5770847A/ja

1981-10-15 Priority to AT81108343T priority patent/ATE10835T1/de

1981-10-15 Priority to DE8181108343T priority patent/DE3167862D1/de

1981-10-15 Priority to EP81108343A priority patent/EP0050799B1/en

1982-05-01 Publication of JPS5770847A publication Critical patent/JPS5770847A/ja

1988-06-28 Publication of JPS6332062B2 publication Critical patent/JPS6332062B2/ja

Status Granted legal-status Critical Current

Links

BBJIPMIXTXKYLZ-UHFFFAOYSA-N isoglutamic acid Chemical compound OC(=O)CC(N)CC(O)=O BBJIPMIXTXKYLZ-UHFFFAOYSA-N 0.000 claims description 18
-1 amine compound Chemical class 0.000 claims description 15
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
150000003863 ammonium salts Chemical class 0.000 claims description 10
150000002148 esters Chemical class 0.000 claims description 9
OXTNCQMOKLOUAM-UHFFFAOYSA-N 3-Oxoglutaric acid Chemical compound OC(=O)CC(=O)CC(O)=O OXTNCQMOKLOUAM-UHFFFAOYSA-N 0.000 claims description 6
229910021529 ammonia Inorganic materials 0.000 claims description 6
239000003513 alkali Substances 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
239000000243 solution Substances 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 15
238000000034 method Methods 0.000 description 10
235000011054 acetic acid Nutrition 0.000 description 9
239000013543 active substance Substances 0.000 description 5
238000000921 elemental analysis Methods 0.000 description 4
239000010410 layer Substances 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical class [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000000126 substance Substances 0.000 description 4
RNJOKCPFLQMDEC-UHFFFAOYSA-N 4(R),8-dimethyl-trans-2-nonenoyl-CoA Chemical compound COC(=O)CC(=O)CC(=O)OC RNJOKCPFLQMDEC-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 3
239000005695 Ammonium acetate Substances 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
235000019257 ammonium acetate Nutrition 0.000 description 3
229940043376 ammonium acetate Drugs 0.000 description 3
SRSPILBBEHNEHD-UHFFFAOYSA-N boranylformonitrile Chemical compound BC#N SRSPILBBEHNEHD-UHFFFAOYSA-N 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
PXJFLUYRGQUUIN-UHFFFAOYSA-N dimethyl 3-aminopentanedioate Chemical compound COC(=O)CC(N)CC(=O)OC PXJFLUYRGQUUIN-UHFFFAOYSA-N 0.000 description 3
238000006722 reduction reaction Methods 0.000 description 3
238000010898 silica gel chromatography Methods 0.000 description 3
238000005160 1H NMR spectroscopy Methods 0.000 description 2
IKHFJPZQZVMLRH-RNFRBKRXSA-N 2-[[[(3r,5r)-3,6-diamino-5-hydroxyhexanoyl]amino]-methylamino]acetic acid Chemical compound OC(=O)CN(C)NC(=O)C[C@H](N)C[C@@H](O)CN IKHFJPZQZVMLRH-RNFRBKRXSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
241000894006 Bacteria Species 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
125000005907 alkyl ester group Chemical group 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
229940088710 antibiotic agent Drugs 0.000 description 2
238000013459 approach Methods 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
150000001576 beta-amino acids Chemical class 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
125000004185 ester group Chemical group 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
239000000203 mixture Substances 0.000 description 2
IKHFJPZQZVMLRH-UHFFFAOYSA-N negamycin Natural products OC(=O)CN(C)NC(=O)CC(N)CC(O)CN IKHFJPZQZVMLRH-UHFFFAOYSA-N 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
WKDDRNSBRWANNC-ATRFCDNQSA-N Thienamycin Chemical compound C1C(SCCN)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 WKDDRNSBRWANNC-ATRFCDNQSA-N 0.000 description 1
WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
YZBQHRLRFGPBSL-RXMQYKEDSA-N carbapenem Chemical class C1C=CN2C(=O)C[C@H]21 YZBQHRLRFGPBSL-RXMQYKEDSA-N 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
BERJDKNLNWRJSZ-UHFFFAOYSA-N diethyl 3-aminopentanedioate Chemical compound CCOC(=O)CC(N)CC(=O)OCC BERJDKNLNWRJSZ-UHFFFAOYSA-N 0.000 description 1
ZSANYRMTSBBUCA-UHFFFAOYSA-N diethyl 3-oxopentanedioate Chemical compound CCOC(=O)CC(=O)CC(=O)OCC ZSANYRMTSBBUCA-UHFFFAOYSA-N 0.000 description 1
OGINYHLEYVNAAR-UHFFFAOYSA-N dimethyl 2-acetylpropanedioate Chemical compound COC(=O)C(C(C)=O)C(=O)OC OGINYHLEYVNAAR-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000012262 fermentative production Methods 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000003541 multi-stage reaction Methods 0.000 description 1
238000007040 multi-step synthesis reaction Methods 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP14634380A 1980-10-21 1980-10-21 Preparation of 3-aminoglutaric acid dialkyl ester Granted JPS5770847A (en)

Priority Applications (4)

Application Number	Priority Date	Filing Date	Title
JP14634380A JPS5770847A (en)	1980-10-21	1980-10-21	Preparation of 3-aminoglutaric acid dialkyl ester
AT81108343T ATE10835T1 (de)	1980-10-21	1981-10-15	Verfahren zur produktion von di-alkylestern und optisch aktiven mono-alkylestern von 3aminoglutars[ure.
DE8181108343T DE3167862D1 (en)	1980-10-21	1981-10-15	New processes for the production of di-alkyl esters and optically active mono-alkyl esters of 3-aminoglutaric acid
EP81108343A EP0050799B1 (en)	1980-10-21	1981-10-15	New processes for the production of di-alkyl esters and optically active mono-alkyl esters of 3-aminoglutaric acid

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP14634380A JPS5770847A (en)	1980-10-21	1980-10-21	Preparation of 3-aminoglutaric acid dialkyl ester

Publications (2)

Publication Number	Publication Date
JPS5770847A JPS5770847A (en)	1982-05-01
JPS6332062B2 true JPS6332062B2 (ko)	1988-06-28

Family

ID=15405548

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP14634380A Granted JPS5770847A (en)	1980-10-21	1980-10-21	Preparation of 3-aminoglutaric acid dialkyl ester

Country Status (1)

Country	Link
JP (1)	JPS5770847A (ko)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0994101A4 (en) *	1997-06-18	2002-05-02	Fujisawa Pharmaceutical Co	NEW PREPARATION PROCESS
KR101299720B1 (ko) *	2006-08-16	2013-08-28	주식회사 엘지생명과학	3-아미노-5-플루오로-4-디알콕시펜탄산 에스테르의 새로운제조방법

1980
- 1980-10-21 JP JP14634380A patent/JPS5770847A/ja active Granted

Also Published As

Publication number	Publication date
JPS5770847A (en)	1982-05-01

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