JPH0768199B2 - グリシンエステル誘導体 - Google Patents

グリシンエステル誘導体

Info

Publication number: JPH0768199B2
Authority: JP; Japan
Prior art keywords: propargyl; compound; formula; general formula; present
Prior art date: 1987-03-24
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 - Lifetime

Application number

JP62070943A

Other languages

English (en)

Japanese (ja)

Other versions

JPS63238052A (ja

Inventor

秀雄香坂

義彦大上

Original Assignee

住友化学工業株式会社

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.)

1987-03-24

Filing date

1987-03-24

Publication date

1995-07-26

1987-03-24 Application filed by 住友化学工業株式会社 filed Critical 住友化学工業株式会社

1987-03-24 Priority to JP62070943A priority Critical patent/JPH0768199B2/ja

1988-03-04 Priority to US07/164,321 priority patent/US4827020A/en

1988-03-07 Priority to EP88301952A priority patent/EP0285270B1/de

1988-03-07 Priority to DE8888301952T priority patent/DE3871591T2/de

1988-03-07 Priority to CA000560680A priority patent/CA1314898C/en

1988-03-23 Priority to DD88313927A priority patent/DD272074A5/de

1988-03-23 Priority to HU881493A priority patent/HU203540B/hu

1988-03-24 Priority to KR1019880003191A priority patent/KR960002371B1/ko

1988-10-04 Publication of JPS63238052A publication Critical patent/JPS63238052A/ja

1995-07-26 Publication of JPH0768199B2 publication Critical patent/JPH0768199B2/ja

2010-07-26 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 title claims description 4
239000004471 Glycine Substances 0.000 title claims description 4
-1 Glycine ester Chemical class 0.000 title description 11
125000000217 alkyl group Chemical group 0.000 claims description 3
150000001875 compounds Chemical class 0.000 description 20
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
238000004519 manufacturing process Methods 0.000 description 7
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
230000000895 acaricidal effect Effects 0.000 description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 4
230000000749 insecticidal effect Effects 0.000 description 4
239000012299 nitrogen atmosphere Substances 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
235000011114 ammonium hydroxide Nutrition 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
SGTIVZMWQGJKAX-UHFFFAOYSA-N methyl 2-[methoxycarbonyl(prop-2-ynyl)amino]acetate Chemical compound COC(=O)CN(CC#C)C(=O)OC SGTIVZMWQGJKAX-UHFFFAOYSA-N 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
VNPSLFACFFRWOZ-UHFFFAOYSA-N 1-prop-2-ynylimidazolidine-2,4-dione Chemical compound O=C1CN(CC#C)C(=O)N1 VNPSLFACFFRWOZ-UHFFFAOYSA-N 0.000 description 2
DZANQNVZHCBOBA-UHFFFAOYSA-N 2-[methoxycarbonyl(prop-2-ynyl)amino]acetic acid Chemical compound COC(=O)N(CC#C)CC(O)=O DZANQNVZHCBOBA-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000007789 gas Substances 0.000 description 2
239000005457 ice water Substances 0.000 description 2
238000000034 method Methods 0.000 description 2
SYMYZVXEVWVLQT-UHFFFAOYSA-N methyl 2-(methoxycarbonylamino)acetate Chemical compound COC(=O)CNC(=O)OC SYMYZVXEVWVLQT-UHFFFAOYSA-N 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
BGDAJAZZHQGIIM-UHFFFAOYSA-N methyl n-(2-aminoacetyl)-n-prop-2-ynylcarbamate Chemical compound COC(=O)N(CC#C)C(=O)CN BGDAJAZZHQGIIM-UHFFFAOYSA-N 0.000 description 2
239000011259 mixed solution Substances 0.000 description 2
YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 2
239000002994 raw material Substances 0.000 description 2
238000010898 silica gel chromatography Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
XSJLQGMTIHCDSS-UHFFFAOYSA-N 2-(prop-2-ynylazaniumyl)acetate Chemical compound OC(=O)CNCC#C XSJLQGMTIHCDSS-UHFFFAOYSA-N 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
239000000642 acaricide Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
125000000304 alkynyl group Chemical group 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000012156 elution solvent Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
LNYUJLIYAHJNNO-UHFFFAOYSA-N ethyl 2-(methoxycarbonylamino)acetate Chemical compound CCOC(=O)CNC(=O)OC LNYUJLIYAHJNNO-UHFFFAOYSA-N 0.000 description 1
NFMKBUMLORTKEX-UHFFFAOYSA-N ethyl 2-[methoxycarbonyl(prop-2-ynyl)amino]acetate Chemical compound CCOC(=O)CN(CC#C)C(=O)OC NFMKBUMLORTKEX-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
PPVUCLAYECHOQZ-UHFFFAOYSA-N imidazolidine-4,5-dione Chemical compound O=C1NCNC1=O PPVUCLAYECHOQZ-UHFFFAOYSA-N 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
LJZPPWWHKPGCHS-UHFFFAOYSA-N propargyl chloride Chemical compound ClCC#C LJZPPWWHKPGCHS-UHFFFAOYSA-N 0.000 description 1
239000002728 pyrethroid Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000007039 two-step reaction Methods 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

JP62070943A 1987-03-24 1987-03-24 グリシンエステル誘導体 Expired - Lifetime JPH0768199B2 (ja)

Priority Applications (8)

Application Number	Priority Date	Filing Date	Title
JP62070943A JPH0768199B2 (ja)	1987-03-24	1987-03-24	グリシンエステル誘導体
US07/164,321 US4827020A (en)	1987-03-24	1988-03-04	Propargyl amide precursor to 1-propargyl-2,4-dioxoimidazolidine
EP88301952A EP0285270B1 (de)	1987-03-24	1988-03-07	Verfahren zur Herstellung von 1-Propargyl-2,4-dioxoimidazolidin
DE8888301952T DE3871591T2 (de)	1987-03-24	1988-03-07	Verfahren zur herstellung von 1-propargyl-2,4-dioxoimidazolidin.
CA000560680A CA1314898C (en)	1987-03-24	1988-03-07	Method for producing 1-propargyl-2,4-dioxoimidazolidine
DD88313927A DD272074A5 (de)	1987-03-24	1988-03-23	Verfahren zur herstellung von 1-propargyl-2,4-dioxo-imidazolidin
HU881493A HU203540B (en)	1987-03-24	1988-03-23	Process for producing 1-propargyl-2,4-dioxo-imidazolidine
KR1019880003191A KR960002371B1 (ko)	1987-03-24	1988-03-24	1-프로파르길-2,4-디옥소이미다졸리딘의 제조중간체 및 그 제조방법

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP62070943A JPH0768199B2 (ja)	1987-03-24	1987-03-24	グリシンエステル誘導体

Publications (2)

Publication Number	Publication Date
JPS63238052A JPS63238052A (ja)	1988-10-04
JPH0768199B2 true JPH0768199B2 (ja)	1995-07-26

Family

ID=13446089

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP62070943A Expired - Lifetime JPH0768199B2 (ja)	1987-03-24	1987-03-24	グリシンエステル誘導体

Country Status (2)

Country	Link
JP (1)	JPH0768199B2 (de)
DD (1)	DD272074A5 (de)

1987
- 1987-03-24 JP JP62070943A patent/JPH0768199B2/ja not_active Expired - Lifetime
1988
- 1988-03-23 DD DD88313927A patent/DD272074A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
DD272074A5 (de)	1989-09-27
JPS63238052A (ja)	1988-10-04

Legal Events

Date	Code	Title	Description
2004-10-18	S531	Written request for registration of change of domicile	Free format text: JAPANESE INTERMEDIATE CODE: R313531
2004-10-18	S533	Written request for registration of change of name	Free format text: JAPANESE INTERMEDIATE CODE: R313533
2004-10-22	R370	Written measure of declining of transfer procedure	Free format text: JAPANESE INTERMEDIATE CODE: R370
2004-11-12	S531	Written request for registration of change of domicile	Free format text: JAPANESE INTERMEDIATE CODE: R313531
2004-11-12	S533	Written request for registration of change of name	Free format text: JAPANESE INTERMEDIATE CODE: R313533
2004-11-19	R350	Written notification of registration of transfer	Free format text: JAPANESE INTERMEDIATE CODE: R350
2007-03-24	EXPY	Cancellation because of completion of term
2007-06-20	FPAY	Renewal fee payment (event date is renewal date of database)	Free format text: PAYMENT UNTIL: 20070726 Year of fee payment: 12

Publication	Publication Date	Title
Shi et al.	1995	. delta.,. epsilon.-Unsaturated. beta.,. beta.-Difluoro-. alpha.-keto Esters: Novel Synthesis and Utility as Precursors of. beta.,. beta.-Difluoro-. alpha.-amino Acids
FR2582309A1 (fr)	1986-11-28	Nouveaux derives du morphinane et de la morphine, leur preparation, leur application comme medicaments et les compositions pharmaceutiques les contenant
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