JPH0452265B2 - - Google Patents
Info
- Publication number
- JPH0452265B2 JPH0452265B2 JP915984A JP915984A JPH0452265B2 JP H0452265 B2 JPH0452265 B2 JP H0452265B2 JP 915984 A JP915984 A JP 915984A JP 915984 A JP915984 A JP 915984A JP H0452265 B2 JPH0452265 B2 JP H0452265B2
- Authority
- JP
- Japan
- Prior art keywords
- cis
- dicarboxylic acid
- acid
- formula
- water
- Prior art date
- 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
Links
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 11
- 239000007864 aqueous solution Substances 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- QSMUFXXTSUEZJA-IYBDPMFKSA-N (4s,5r)-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid Chemical compound N1([C@@H]([C@@H](N(C1=O)CC=1C=CC=CC=1)C(=O)O)C(O)=O)CC1=CC=CC=C1 QSMUFXXTSUEZJA-IYBDPMFKSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
- 150000007517 lewis acids Chemical class 0.000 description 3
- 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 3
- LUMVCLJFHCTMCV-UHFFFAOYSA-M potassium;hydroxide;hydrate Chemical compound O.[OH-].[K+] LUMVCLJFHCTMCV-UHFFFAOYSA-M 0.000 description 3
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- XTMPFXTWTYPFSH-UHFFFAOYSA-N 2-oxoimidazolidine-4,5-dicarboxylic acid Chemical compound OC(=O)C1NC(=O)NC1C(O)=O XTMPFXTWTYPFSH-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000011736 potassium bicarbonate Substances 0.000 description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- JBJWASZNUJCEKT-UHFFFAOYSA-M sodium;hydroxide;hydrate Chemical compound O.[OH-].[Na+] JBJWASZNUJCEKT-UHFFFAOYSA-M 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- -1 alkyl chlorocarbonate Chemical compound 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229960002685 biotin Drugs 0.000 description 1
- 235000020958 biotin Nutrition 0.000 description 1
- 239000011616 biotin Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003814 drug Substances 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
- 238000000605 extraction Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP915984A JPS60152469A (ja) | 1984-01-21 | 1984-01-21 | シス−ジエステル体の製造方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP915984A JPS60152469A (ja) | 1984-01-21 | 1984-01-21 | シス−ジエステル体の製造方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS60152469A JPS60152469A (ja) | 1985-08-10 |
JPH0452265B2 true JPH0452265B2 (pt) | 1992-08-21 |
Family
ID=11712835
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP915984A Granted JPS60152469A (ja) | 1984-01-21 | 1984-01-21 | シス−ジエステル体の製造方法 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS60152469A (pt) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006232743A (ja) * | 2005-02-25 | 2006-09-07 | Sumitomo Chemical Co Ltd | 1,3−ジベンジル−2−オキソイミダゾリジン−4,5−ジカルボン酸ジメチルの製造方法 |
CN105399677B (zh) * | 2015-11-17 | 2019-02-22 | 蚌埠丰原医药科技发展有限公司 | 一种反式环酸的制备方法 |
CN106905239A (zh) * | 2017-03-15 | 2017-06-30 | 安徽泰格维生素实业有限公司 | 一种双苄基二羧酸的精制方法 |
-
1984
- 1984-01-21 JP JP915984A patent/JPS60152469A/ja active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS60152469A (ja) | 1985-08-10 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
SU791246A3 (ru) | Способ получени производных 7-/2-(2аминотиазолил-4)-2-алкоксииминоацетамидо/-3-цефем-4-карбоновой кислоты | |
WO1999016742A1 (en) | Processes and intermediates useful to make antifolates | |
US6262262B1 (en) | Processes and intermediates useful to make antifolates | |
EP0413064A1 (en) | Preparation of 2-phenyl-1, 3-propane diol and its dicarbamate | |
JPS626718B2 (pt) | ||
JPH0452265B2 (pt) | ||
KR100377718B1 (ko) | 매트릭스 메탈로프로테이나제 저해제의 제조에 유용한장애 설폰아미드의 알킬화 방법 | |
CN110551123A (zh) | 一种5-(叔丁氧羰基)-2-甲基-4,5,6,7-四氢-2h-吡唑并[4,3-c]吡啶-7-羧酸的制备方法 | |
US7109353B2 (en) | Process for preparing 5,6-dihydro-4-(S)-(ethylamino)-6-(S) methyl-4H-thieno[2,3b]thiopyran-2-sulphonamide-7,7-dioxide HCl | |
EP0905128A1 (en) | Processes and intermediates useful to make antifolates | |
US6225480B1 (en) | Sulphonyl compounds for use as linkers in solid phase and combinatorial synthesis | |
CN113831237A (zh) | 一种9-蒽甲酸的合成方法 | |
US4948916A (en) | Process for producing aminooxyacetic acid salts | |
US4154757A (en) | Process for the manufacture of p-hydroxybenzyl cyanide | |
JPH0421674A (ja) | 2―クロロ―5―(アミノメチル)チアゾールの製造方法 | |
JPS6338355B2 (pt) | ||
JPS60172975A (ja) | エリスロ−3−(3,4−メチレンジオキシフエニル)セリンの製造方法 | |
US6090168A (en) | Processes and intermediates useful to make antifolates | |
KR101170192B1 (ko) | 1,2-벤즈이속사졸-3-메탄술폰아미드의 원-포트 제조방법 | |
JP2855871B2 (ja) | チオリンゴ酸の製造方法 | |
KR100187734B1 (ko) | 지방족 아미드 및 그의 염의 제조 방법 | |
SU1077881A1 (ru) | Способ получени @ -циклогексилоксикарбонильных производных аминокислот | |
EP0104721B1 (en) | Process for the preparation of 2-chlorosulfonyl-4-(n-substituted sulfamyl)-chlorobenzene compounds | |
US4571429A (en) | Process for the preparation of o-carboethoxybenzenesulfonamide | |
SU1705286A1 (ru) | Способ получени 3-алкилзамещенных 4-гидроксихинолин-2-онов |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
LAPS | Cancellation because of no payment of annual fees |