IE42206B1 - Optical resolution of 1-t-butylamino -2,3-dihydroxypropane - Google Patents
Optical resolution of 1-t-butylamino -2,3-dihydroxypropaneInfo
- Publication number
- IE42206B1 IE42206B1 IE2702/75A IE270275A IE42206B1 IE 42206 B1 IE42206 B1 IE 42206B1 IE 2702/75 A IE2702/75 A IE 2702/75A IE 270275 A IE270275 A IE 270275A IE 42206 B1 IE42206 B1 IE 42206B1
- Authority
- IE
- Ireland
- Prior art keywords
- butylamino
- dihydroxypropane
- diastereoisomer
- solution
- tartaric acid
- Prior art date
Links
- JWBMVCAZXJMSOX-UHFFFAOYSA-N 3-(tert-butylamino)propane-1,2-diol Chemical compound CC(C)(C)NCC(O)CO JWBMVCAZXJMSOX-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 230000003287 optical effect Effects 0.000 title abstract description 3
- ODHCTXKNWHHXJC-GSVOUGTGSA-N 5-oxo-D-proline Chemical compound OC(=O)[C@H]1CCC(=O)N1 ODHCTXKNWHHXJC-GSVOUGTGSA-N 0.000 claims abstract description 23
- 239000000203 mixture Substances 0.000 claims abstract description 21
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 13
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims abstract description 13
- FEWJPZIEWOKRBE-LWMBPPNESA-N levotartaric acid Chemical compound OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 claims abstract description 10
- 239000007787 solid Substances 0.000 claims abstract description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 19
- ODHCTXKNWHHXJC-UHFFFAOYSA-N acide pyroglutamique Natural products OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 claims description 19
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 239000001358 L(+)-tartaric acid Substances 0.000 claims description 9
- 235000011002 L(+)-tartaric acid Nutrition 0.000 claims description 9
- JWBMVCAZXJMSOX-ZCFIWIBFSA-N (2r)-3-(tert-butylamino)propane-1,2-diol Chemical compound CC(C)(C)NC[C@@H](O)CO JWBMVCAZXJMSOX-ZCFIWIBFSA-N 0.000 claims description 7
- AUONNNVJUCSETH-UHFFFAOYSA-N icosanoyl icosanoate Chemical compound CCCCCCCCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCCCCCCCC AUONNNVJUCSETH-UHFFFAOYSA-N 0.000 claims description 6
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 claims description 4
- 235000002906 tartaric acid Nutrition 0.000 claims description 2
- 239000011975 tartaric acid Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 13
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 abstract description 4
- 239000003456 ion exchange resin Substances 0.000 abstract description 3
- 229920003303 ion-exchange polymer Polymers 0.000 abstract description 3
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 abstract description 3
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 abstract 1
- 229960001270 d- tartaric acid Drugs 0.000 abstract 1
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002876 beta blocker Substances 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- -1 3 - substituted - 4 - (3 - t - butylamino - 2hydroxypropoxy) - 1,2,5 - thiadiazole Chemical class 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 229940030611 beta-adrenergic blocking agent Drugs 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- MJJYBIKJATXOSF-YFKPBYRVSA-N (2r)-2,3-dihydroxy-4-methylpent-3-enal Chemical compound CC(C)=C(O)[C@@H](O)C=O MJJYBIKJATXOSF-YFKPBYRVSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- YSKMEMRDVDKQES-UHFFFAOYSA-N 3-amino-4,4-dimethylpentane-1,2-diol Chemical compound CC(C)(C)C(N)C(O)CO YSKMEMRDVDKQES-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- JGFBQFKZKSSODQ-UHFFFAOYSA-N Isothiocyanatocyclopropane Chemical compound S=C=NC1CC1 JGFBQFKZKSSODQ-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000674 adrenergic antagonist Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 229940097320 beta blocking agent Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- PWLNAUNEAKQYLH-UHFFFAOYSA-N butyric acid octyl ester Natural products CCCCCCCCOC(=O)CCC PWLNAUNEAKQYLH-UHFFFAOYSA-N 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- CIBMHJPPKCXONB-UHFFFAOYSA-N propane-2,2-diol Chemical compound CC(C)(O)O CIBMHJPPKCXONB-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
- C07C215/10—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic with one amino group and at least two hydroxy groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B53/00—Asymmetric syntheses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B57/00—Separation of optically-active compounds
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 |
|---|---|---|---|
| US53254774A | 1974-12-13 | 1974-12-13 | |
| US61594175A | 1975-09-25 | 1975-09-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE42206L IE42206L (en) | 1976-06-13 |
| IE42206B1 true IE42206B1 (en) | 1980-06-18 |
Family
ID=27063872
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2702/75A IE42206B1 (en) | 1974-12-13 | 1975-12-11 | Optical resolution of 1-t-butylamino -2,3-dihydroxypropane |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS51118711A (enExample) |
| AU (1) | AU510799B2 (enExample) |
| CA (1) | CA1064943A (enExample) |
| DE (1) | DE2556040C2 (enExample) |
| DK (1) | DK532575A (enExample) |
| FR (2) | FR2294151A1 (enExample) |
| GB (1) | GB1470030A (enExample) |
| IE (1) | IE42206B1 (enExample) |
| NL (1) | NL7513818A (enExample) |
| SE (1) | SE435499B (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5931693A (ja) * | 1982-08-13 | 1984-02-20 | Kanegafuchi Chem Ind Co Ltd | 光学活性オキサゾリジノン誘導体の製造方法 |
| JPH01149775A (ja) * | 1987-12-07 | 1989-06-12 | Kawaken Fine Chem Co Ltd | 光学活性２−メチルピペラジンの製造方法 |
| US5684159A (en) * | 1995-05-30 | 1997-11-04 | Rhone-Poulenc Rorer S.A. | L-tartaric acid salt of a (1R) diastereomer of a 2-azadihydroxybicyclo 2.2.1!heptane compound and the preparation of 2-azabicyclo 2.2.1!heptane compounds |
| IN187238B (enExample) * | 1995-06-30 | 2002-03-09 | Astra Ab | |
| JP7603368B2 (ja) | 2016-03-25 | 2024-12-20 | ザ ユナイテッド ステイツ オブ アメリカ， アズ リプレゼンテッド バイ ザ セクレタリー， デパートメント オブ ヘルス アンド ヒューマン サービシーズ | （２ｒ，６ｒ）－ヒドロキシノルケタミン塩酸塩の結晶形態 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2528267A (en) * | 1950-10-31 | Eobeet j | ||
| US3116332A (en) * | 1958-10-17 | 1963-12-31 | Du Pont | Resolution of racemic aminoisopropanol |
-
1975
- 1975-11-26 NL NL7513818A patent/NL7513818A/xx active Search and Examination
- 1975-11-26 DK DK532575A patent/DK532575A/da not_active Application Discontinuation
- 1975-11-26 SE SE7513307A patent/SE435499B/xx not_active IP Right Cessation
- 1975-12-03 AU AU87220/75A patent/AU510799B2/en not_active Expired
- 1975-12-08 CA CA241,257A patent/CA1064943A/en not_active Expired
- 1975-12-09 FR FR7537575A patent/FR2294151A1/fr active Granted
- 1975-12-10 GB GB5063275A patent/GB1470030A/en not_active Expired
- 1975-12-11 IE IE2702/75A patent/IE42206B1/en unknown
- 1975-12-12 JP JP50147481A patent/JPS51118711A/ja active Pending
- 1975-12-12 DE DE2556040A patent/DE2556040C2/de not_active Expired
-
1976
- 1976-05-04 FR FR7613241A patent/FR2303790A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2303790B1 (enExample) | 1980-07-18 |
| FR2294151A1 (fr) | 1976-07-09 |
| AU510799B2 (en) | 1980-07-17 |
| DE2556040A1 (de) | 1976-06-16 |
| JPS51118711A (en) | 1976-10-18 |
| SE7513307L (sv) | 1976-06-14 |
| GB1470030A (en) | 1977-04-14 |
| DE2556040C2 (de) | 1986-05-07 |
| SE435499B (sv) | 1984-10-01 |
| DK532575A (da) | 1976-06-14 |
| IE42206L (en) | 1976-06-13 |
| FR2303790A1 (fr) | 1976-10-08 |
| CA1064943A (en) | 1979-10-23 |
| AU8722075A (en) | 1977-06-09 |
| NL7513818A (nl) | 1976-06-15 |
| FR2294151B1 (enExample) | 1979-04-06 |
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