JPS6144852A - ｔｅｒｔ−ブチルγ−ジメチルアミノβ−ヒドロキシブチレ−トおよびその製法 - Google Patents
ｔｅｒｔ−ブチルγ−ジメチルアミノβ−ヒドロキシブチレ−トおよびその製法Info
- Publication number
- JPS6144852A JPS6144852A JP60148145A JP14814585A JPS6144852A JP S6144852 A JPS6144852 A JP S6144852A JP 60148145 A JP60148145 A JP 60148145A JP 14814585 A JP14814585 A JP 14814585A JP S6144852 A JPS6144852 A JP S6144852A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- tert
- represented
- tables
- formulas
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 title description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- RJUIDDKTATZJFE-NSCUHMNNSA-N (e)-but-2-enoyl chloride Chemical compound C\C=C\C(Cl)=O RJUIDDKTATZJFE-NSCUHMNNSA-N 0.000 claims description 7
- 239000004593 Epoxy Substances 0.000 claims description 7
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
- 239000012044 organic layer Substances 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- NGASWKRTXGWPNN-UHFFFAOYSA-N tert-butyl but-3-enoate Chemical compound CC(C)(C)OC(=O)CC=C NGASWKRTXGWPNN-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 125000005233 alkylalcohol group Chemical group 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims description 3
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims description 3
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 claims description 2
- 239000012298 atmosphere Substances 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- PHIQHXFUZVPYII-ZCFIWIBFSA-O (R)-carnitinium Chemical compound C[N+](C)(C)C[C@H](O)CC(O)=O PHIQHXFUZVPYII-ZCFIWIBFSA-O 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 229960004203 carnitine Drugs 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000010907 mechanical stirring Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- MAUMSNABMVEOGP-UHFFFAOYSA-N (methyl-$l^{2}-azanyl)methane Chemical compound C[N]C MAUMSNABMVEOGP-UHFFFAOYSA-N 0.000 description 1
- NXDDNODAJKZARA-UHFFFAOYSA-N 4-(dimethylazaniumyl)-3-hydroxybutanoate Chemical compound CN(C)CC(O)CC(O)=O NXDDNODAJKZARA-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- RDHQFKQIGNGIED-MRVPVSSYSA-N O-acetyl-L-carnitine Chemical compound CC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C RDHQFKQIGNGIED-MRVPVSSYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 229960001009 acetylcarnitine Drugs 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- VDQVEACBQKUUSU-UHFFFAOYSA-M disodium;sulfanide Chemical compound [Na+].[Na+].[SH-] VDQVEACBQKUUSU-UHFFFAOYSA-M 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- -1 tert-butyl vinyl Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C219/06—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having the hydroxy groups esterified by carboxylic acids having the esterifying carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D303/40—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals by ester radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT48504/84A IT1177875B (it) | 1984-07-04 | 1984-07-04 | Gamma dimetilamino beta-idrossi butirrato di terz-butile e procedimento per la sua preparazione |
| IT48504A/84 | 1984-07-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6144852A true JPS6144852A (ja) | 1986-03-04 |
Family
ID=11266961
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60148145A Pending JPS6144852A (ja) | 1984-07-04 | 1985-07-04 | ｔｅｒｔ−ブチルγ−ジメチルアミノβ−ヒドロキシブチレ−トおよびその製法 |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0169176A1 (en, 2012) |
| JP (1) | JPS6144852A (en, 2012) |
| KR (1) | KR860001053A (en, 2012) |
| CA (1) | CA1251464A (en, 2012) |
| DK (1) | DK301785A (en, 2012) |
| GR (1) | GR851622B (en, 2012) |
| IL (1) | IL75626A (en, 2012) |
| IT (1) | IT1177875B (en, 2012) |
| PT (1) | PT80756B (en, 2012) |
| YU (1) | YU103985A (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1184284B (it) * | 1985-06-28 | 1987-10-22 | Sigma Tau Ind Farmaceuti | Procedimento per la preparazione di r(-)-norcarnitina terz-butil estere |
-
1984
- 1984-07-04 IT IT48504/84A patent/IT1177875B/it active
-
1985
- 1985-06-20 KR KR1019850004375A patent/KR860001053A/ko not_active Withdrawn
- 1985-06-21 EP EP85830156A patent/EP0169176A1/en not_active Withdrawn
- 1985-06-21 YU YU01039/85A patent/YU103985A/xx unknown
- 1985-06-21 CA CA000484754A patent/CA1251464A/en not_active Expired
- 1985-06-25 IL IL75626A patent/IL75626A/xx unknown
- 1985-07-02 GR GR851622A patent/GR851622B/el unknown
- 1985-07-02 DK DK301785A patent/DK301785A/da unknown
- 1985-07-03 PT PT80756A patent/PT80756B/pt unknown
- 1985-07-04 JP JP60148145A patent/JPS6144852A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| PT80756B (en) | 1987-02-11 |
| PT80756A (en) | 1985-08-01 |
| GR851622B (en, 2012) | 1985-11-26 |
| DK301785A (da) | 1986-01-05 |
| IT1177875B (it) | 1987-08-26 |
| YU103985A (en) | 1987-12-31 |
| EP0169176A1 (en) | 1986-01-22 |
| DK301785D0 (da) | 1985-07-02 |
| CA1251464A (en) | 1989-03-21 |
| KR860001053A (ko) | 1986-02-22 |
| IL75626A0 (en) | 1985-10-31 |
| IL75626A (en) | 1990-04-29 |
| IT8448504A0 (it) | 1984-07-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1340549C (en) | Method of preparing sphingosine derivatives | |
| JPS6323834A (ja) | マロン酸誘導体 | |
| US4910326A (en) | β-ketonitrils | |
| HU185330B (en) | Process for preparing /+/-4-substituted-2-indazoles | |
| JPS6144852A (ja) | ｔｅｒｔ−ブチルγ−ジメチルアミノβ−ヒドロキシブチレ−トおよびその製法 | |
| US3910958A (en) | Process for preparing arylacetic acids and esters thereof | |
| Youn et al. | Highly diastereoselective additions of methoxyallene and acetylenes to chiral α-keto amidesElectronic supplementary information (ESI) available: synthesis and spectroscopic data for 4b, 5g, 6b and 7b. See http://www. rsc. org/suppdata/cc/b1/b100355k | |
| SU1215619A3 (ru) | Способ получени сложных эфиров @ -алкилтартроновой или @ -галогеналкилтартроновой кислот | |
| US4116970A (en) | N-2-hydroxyethyl-oxazolidine compound | |
| JPS5840938B2 (ja) | 置換又は未置換α−オキシコハク酸エステルの製造方法 | |
| JPH0142254B2 (en, 2012) | ||
| EP0677525A1 (fr) | Dérivés d'acides aminoboroniques, leur préparation et leur utilisation comme intermédiaires de synthèse | |
| JPH062747B2 (ja) | ２‐アルキル‐４，５‐ジヒドロキシメチルイミダゾールの製法 | |
| BG60580B1 (bg) | Метод за получаване на 2,2-диметил-5-(2,5-диметилфенокси)- пентанова киселина,междинни съединения за получаването й и метод за получаване на междинните съединения | |
| JP2622747B2 (ja) | シス―７―デセン―４―オリドの製造方法 | |
| EP0101004A1 (en) | Process for preparing 4-oxo-4, 5, 6, 7-tetrahydroindole derivative | |
| US5146003A (en) | 3-amino-2-hydroxybornane derivatives, asymmetric michael reaction using the same, and process for preparing optically active muscone utilizing michael reaction | |
| US4249015A (en) | Preparation of organic acids and/or esters | |
| US4188343A (en) | Process for preparing anthranylaldehyde derivatives | |
| JP3634874B2 (ja) | トリフルオロメチルアセチレン誘導体、その製造方法およびその中間体の製造方法 | |
| US4487721A (en) | Process for producing 2-amino-2-arylacetonitriles | |
| SU1142470A1 (ru) | Способ получени арилгидразидов @ , @ -дизамещенных акриловых кислот | |
| JPS6219582A (ja) | γ−チオブチロラクトン誘導体の製造方法 | |
| JPS6383039A (ja) | 脂環式ケトンの製造法 | |
| HU193454B (en) | Process for producing 3-phenyl-butyraldehyde derivatives |