JPH0374218B2 - - Google Patents

Info

Publication number: JPH0374218B2
Authority: JP; Japan
Prior art keywords: dimethoxy; mol; reaction; added; triazine
Prior art date: 1983-11-17
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

JP21508483A

Other languages

English (en)

Japanese (ja)

Other versions

JPS60109576A (ja

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.)

1983-11-17

Filing date

1983-11-17

Publication date

1991-11-26

1983-11-17 Application filed filed Critical

1983-11-17 Priority to JP21508483A priority Critical patent/JPS60109576A/ja

1985-06-15 Publication of JPS60109576A publication Critical patent/JPS60109576A/ja

1991-11-26 Publication of JPH0374218B2 publication Critical patent/JPH0374218B2/ja

Status Granted legal-status Critical Current

Links

-1 2-(4-methoxybenzyloxycarbonylthio)-4,6-dimethoxy-1,3,5-triazine Chemical compound 0.000 claims description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
239000003153 chemical reaction reagent Substances 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
238000000034 method Methods 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 5
238000001816 cooling Methods 0.000 description 5
FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 4
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
239000013078 crystal Substances 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
LXWWMGRGWJGVRE-UHFFFAOYSA-N 4,6-dimethoxy-2H-triazine-5-thione Chemical compound SC=1C(=NN=NC1OC)OC LXWWMGRGWJGVRE-UHFFFAOYSA-N 0.000 description 3
MSHFRERJPWKJFX-UHFFFAOYSA-N 4-Methoxybenzyl alcohol Chemical compound COC1=CC=C(CO)C=C1 MSHFRERJPWKJFX-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
229960003767 alanine Drugs 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
239000007788 liquid Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
239000002994 raw material Substances 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 2
239000004471 Glycine Substances 0.000 description 2
QNAYBMKLOCPYGJ-UWTATZPHSA-N L-Alanine Natural products C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 description 2
QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
238000007664 blowing Methods 0.000 description 2
238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
229910001873 dinitrogen Inorganic materials 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000012454 non-polar solvent Substances 0.000 description 2
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-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
238000000746 purification Methods 0.000 description 2
230000007017 scission Effects 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
URMGKEIMVQSNIY-UHFFFAOYSA-N 2,6-dimethoxy-1h-1,3,5-triazine-4-thione Chemical compound COC1=NC(S)=NC(OC)=N1 URMGKEIMVQSNIY-UHFFFAOYSA-N 0.000 description 1
DKEFXDVVCVXQNW-UHFFFAOYSA-N 2-[(4-methoxyphenyl)methoxycarbonylamino]acetic acid Chemical compound COC1=CC=C(COC(=O)NCC(O)=O)C=C1 DKEFXDVVCVXQNW-UHFFFAOYSA-N 0.000 description 1
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
GMUCTPMXBBPDSS-UHFFFAOYSA-N O1CCOCC1.N1=NN=CC=C1 Chemical compound O1CCOCC1.N1=NN=CC=C1 GMUCTPMXBBPDSS-UHFFFAOYSA-N 0.000 description 1
IPRBOQUKBZNCAG-UHFFFAOYSA-N [[cyano(phenyl)methylidene]amino] (4-methoxyphenyl)methyl carbonate Chemical compound C1=CC(OC)=CC=C1COC(=O)ON=C(C#N)C1=CC=CC=C1 IPRBOQUKBZNCAG-UHFFFAOYSA-N 0.000 description 1
238000000862 absorption spectrum Methods 0.000 description 1
229940024606 amino acid Drugs 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
238000010647 peptide synthesis reaction Methods 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
239000000047 product Substances 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007858 starting material Substances 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
239000010409 thin film Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1

Landscapes

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

JP21508483A 1983-11-17 1983-11-17 新規なｐ−メトキシベンジルオキシカルボニル基を有する化合物 Granted JPS60109576A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP21508483A JPS60109576A (ja)	1983-11-17	1983-11-17	新規なｐ−メトキシベンジルオキシカルボニル基を有する化合物

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP21508483A JPS60109576A (ja)	1983-11-17	1983-11-17	新規なｐ−メトキシベンジルオキシカルボニル基を有する化合物

Publications (2)

Publication Number	Publication Date
JPS60109576A JPS60109576A (ja)	1985-06-15
JPH0374218B2 true JPH0374218B2 (cs)	1991-11-26

Family

ID=16666481

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP21508483A Granted JPS60109576A (ja)	1983-11-17	1983-11-17	新規なｐ−メトキシベンジルオキシカルボニル基を有する化合物

Country Status (1)

Country	Link
JP (1)	JPS60109576A (cs)

1983
- 1983-11-17 JP JP21508483A patent/JPS60109576A/ja active Granted

Also Published As

Publication number	Publication date
JPS60109576A (ja)	1985-06-15

Publication	Publication Date	Title
US6613908B2 (en)	2003-09-02	Method for carbamoylating alcohols
Kim et al.	1985	New amino-protective reagents for t-butoxycarbonylation and benzyloxycarbonylation of amines and amino acids.
US3487070A (en)	1969-12-30	3-blocked amino-4-sulfhydryl-2-azetidinones
JPS6272662A (ja)	1987-04-03	４−アルコキシ−３−ピロリン−２−オン−１−イル−酢酸アルキルエステルおよびその製造方法
KR100708581B1 (ko)	2007-04-18	리토나비르의 합성 방법
JPS60109576A (ja)	1985-06-15	新規なｐ−メトキシベンジルオキシカルボニル基を有する化合物
JP5279449B2 (ja)	2013-09-04	５−｛４−［２−（５−エチル−２−ピリジル）エトキシ］ベンジル｝−２，４−チアゾリジンジオン塩酸塩の製造方法
JP2815438B2 (ja)	1998-10-27	１，２―ビス（ニコチンアミド）プロパンの精製方法
JPS6126908B2 (cs)	1986-06-23
JPS6047261B2 (ja)	1985-10-21	新規なチオ−ルカルボネ−トおよびその製造
KR950007921B1 (ko)	1995-07-21	피라졸 설포닐이소시아네이트 유도체의 제조방법
US5099022A (en)	1992-03-24	Process for purification of 1,2-bis(nicotinamido)propane
KR960007530B1 (ko)	1996-06-05	설포닐우레아 유도체의 제조방법
KR950000470B1 (ko)	1995-01-20	β-치환된-N-카르보벤족시-L-아스파르테이트의 제조방법
JPS6136261A (ja)	1986-02-20	新規炭酸エステル化合物およびその製造方法
SU876641A1 (ru)	1981-10-30	Производные S-пирролидонметил-цистеина в качестве промежуточных продуктов дл синтеза цистинсодержащих пептидов
JPS60115567A (ja)	1985-06-22	３−アミノイソオキサゾ−ル類の製法
KR810000454B1 (ko)	1981-05-02	치환 안식향산아미드 유도체의 제조방법
NO180416B (no)	1997-01-06	Fremgangsmåte for fremstilling av et alifatisk amid og salter derav
EP0493813A1 (en)	1992-07-08	2,5-Dioxopiperazine compound and processes for preparation thereof
JPH0327546B2 (cs)	1991-04-16
JPS5916879A (ja)	1984-01-28	Ｎ−置換イミダゾ−ル類の製造法
JPS607623B2 (ja)	1985-02-26	１―カルバモイル―５―フルオロウラシル誘導体およびその製造法
JPS60116674A (ja)	1985-06-24	５−アミノイソオキサゾ−ルの製法
EP0239354A2 (en)	1987-09-30	2,2-Dinitrophenylethane derivatives and their application as protecting compounds