JPS59190955A - アミノ酸ラセミ体の分割 - Google Patents

アミノ酸ラセミ体の分割

Info

Publication number: JPS59190955A
Authority: JP; Japan
Prior art keywords: amino acid; optically active; menthol; amino acids; diastereomers
Prior art date: 1983-04-11
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.): Granted

Application number

JP6350983A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6335620B2 (da

Inventor

デビツド・ワ−ス・ハウス

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Honeywell UOP LLC

Original Assignee

UOP LLC

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.)

1983-04-11

Filing date

1983-04-11

Publication date

1984-10-29

1983-04-11 Application filed by UOP LLC filed Critical UOP LLC

1983-04-11 Priority to JP6350983A priority Critical patent/JPS59190955A/ja

1984-10-29 Publication of JPS59190955A publication Critical patent/JPS59190955A/ja

1988-07-15 Publication of JPS6335620B2 publication Critical patent/JPS6335620B2/ja

Status Granted legal-status Critical Current

Links

150000001413 amino acids Chemical class 0.000 title claims description 40
NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 claims description 23
238000000034 method Methods 0.000 claims description 23
NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 claims description 21
150000002148 esters Chemical class 0.000 claims description 19
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 14
229940041616 menthol Drugs 0.000 claims description 13
239000002904 solvent Substances 0.000 claims description 13
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 8
230000007062 hydrolysis Effects 0.000 claims description 4
238000006460 hydrolysis reaction Methods 0.000 claims description 4
239000000377 silicon dioxide Substances 0.000 claims description 4
WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims description 3
WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims description 2
239000003377 acid catalyst Substances 0.000 claims description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
239000003054 catalyst Substances 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
239000010457 zeolite Substances 0.000 claims description 2
229910021536 Zeolite Inorganic materials 0.000 claims 1
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims 1
229940024606 amino acid Drugs 0.000 description 34
235000001014 amino acid Nutrition 0.000 description 33
239000003480 eluent Substances 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
238000000926 separation method Methods 0.000 description 11
239000000203 mixture Substances 0.000 description 7
239000000243 solution Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 5
-1 amino acid enantiomers Chemical class 0.000 description 5
NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 4
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 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
239000012071 phase Substances 0.000 description 4
229960005190 phenylalanine Drugs 0.000 description 4
COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
230000005526 G1 to G0 transition Effects 0.000 description 3
OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000013375 chromatographic separation Methods 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
QKGYJVXSKCDGOK-UHFFFAOYSA-N hexane;propan-2-ol Chemical compound CC(C)O.CCCCCC QKGYJVXSKCDGOK-UHFFFAOYSA-N 0.000 description 3
230000003287 optical effect Effects 0.000 description 3
230000000717 retained effect Effects 0.000 description 3
238000004366 reverse phase liquid chromatography Methods 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
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MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 2
KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
241000951471 Citrus junos Species 0.000 description 2
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-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
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
LJCWONGJFPCTTL-ZETCQYMHSA-N L-4-hydroxyphenylglycine Chemical compound OC(=O)[C@@H](N)C1=CC=C(O)C=C1 LJCWONGJFPCTTL-ZETCQYMHSA-N 0.000 description 2
ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 description 2
QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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238000010521 absorption reaction Methods 0.000 description 2
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150000007513 acids Chemical class 0.000 description 2
239000002585 base Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
238000007429 general method Methods 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
239000000463 material Substances 0.000 description 2
BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
238000010992 reflux Methods 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000002002 slurry Substances 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
229910001220 stainless steel Inorganic materials 0.000 description 2
239000010935 stainless steel Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
ILDUDDMQRRPQIP-HFCFLWKCSA-N (1-methyl-4-propan-2-ylcyclohexyl) (2S)-2-amino-3-phenylpropanoate Chemical compound C1(CCC(CC1)C(C)C)(C)OC([C@@H](N)CC1=CC=CC=C1)=O ILDUDDMQRRPQIP-HFCFLWKCSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
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FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1

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

JP6350983A 1983-04-11 1983-04-11 アミノ酸ラセミ体の分割 Granted JPS59190955A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP6350983A JPS59190955A (ja)	1983-04-11	1983-04-11	アミノ酸ラセミ体の分割

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP6350983A JPS59190955A (ja)	1983-04-11	1983-04-11	アミノ酸ラセミ体の分割

Publications (2)

Publication Number	Publication Date
JPS59190955A true JPS59190955A (ja)	1984-10-29
JPS6335620B2 JPS6335620B2 (da)	1988-07-15

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ID=13231263

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP6350983A Granted JPS59190955A (ja)	1983-04-11	1983-04-11	アミノ酸ラセミ体の分割

Country Status (1)

Country	Link
JP (1)	JPS59190955A (da)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6355557A (ja) *	1986-04-18	1988-03-10	Hitachi Ltd	電子写真感光体
JPH01221331A (ja) *	1988-02-29	1989-09-04	Daicel Chem Ind Ltd	分離方法
JPH01290635A (ja) *	1988-05-18	1989-11-22	Daicel Chem Ind Ltd	光学分割方法

1983
- 1983-04-11 JP JP6350983A patent/JPS59190955A/ja active Granted

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6355557A (ja) *	1986-04-18	1988-03-10	Hitachi Ltd	電子写真感光体
JPH01221331A (ja) *	1988-02-29	1989-09-04	Daicel Chem Ind Ltd	分離方法
JPH01290635A (ja) *	1988-05-18	1989-11-22	Daicel Chem Ind Ltd	光学分割方法

Also Published As

Publication number	Publication date
JPS6335620B2 (da)	1988-07-15

Publication	Publication Date	Title
EP0737182A1 (en)	1996-10-16	Process for the preparation of an optically pure enantiomer of formoterol
Bergot et al.	1978	Liquid chromatographic analysis of enantiomeric purity of several terpenoid acids as their 1-(1-naphthyl) ethylamide derivatives
US4418225A (en)	1983-11-29	Resolution of d,1-menthol
KR100790507B1 (ko)	2008-01-02	아미노산 유도체의 광학 이성체의 분리 방법
JPS63218857A (ja)	1988-09-12	液体クロマトグラフイ−用充てん剤
CN110845349B (zh)	2020-11-24	一种沙库巴曲缬沙坦钠中间体的纯化方法
JPS59190955A (ja)	1984-10-29	アミノ酸ラセミ体の分割
US4379941A (en)	1983-04-12	Resolution of racemic amino acids
US4524223A (en)	1985-06-18	Resolution of alcohols using amino acids
EP0121618A1 (en)	1984-10-17	A method for the resolution of racemic amino acids
KR101067314B1 (ko)	2011-09-23	3,5-디하이드록시-6-헵테노에이트 제조 방법
JPH0632787A (ja)	1994-02-08	プロピオン酸誘導体の製造法
JPS6187640A (ja)	1986-05-06	分離法
GB2272218A (en)	1994-05-11	Process for the preparation of l-5-(2- - acetoxy-propionylamino)-2,4,6-triiodoisophthalic acid bis-(1,3-dihydroxy-propylamide)
JPS6123177B2 (da)	1986-06-04
JPS63501507A (ja)	1988-06-09	光学活性試薬および対掌体アミン化合物の測定法
JPH0816084B2 (ja)	1996-02-21	光学活性フェニルエチルアミン誘導体の製造法
JP2912075B2 (ja)	1999-06-28	ガスクロマトグラフィー用充填剤
Julia et al.	1979	Resolution of Racemic Modifications by Gas-Liquid Chromatography via the Separation of Diastereoisomeric Esters. VII. Cyanohydrins
EP0260668A2 (en)	1988-03-23	Separation of diastereomers
JP4067319B2 (ja)	2008-03-26	光学分割法及び光学活性化合物の製造法
Horiba et al.	1982	Absolute Configurational Studies of Arylalkylamines by Circular Dichroism Measurements and Gas Chromatography
JP2912078B2 (ja)	1999-06-28	ガスクロマトグラフィー用光学活性カラム充填剤
JPH089554B2 (ja)	1996-01-31	光学分割法
JPH0751551B2 (ja)	1995-06-05	Ｎ−ステアロイル−Ｌ−バリンｔ−ブチルアミド及びその用途

JPS59190955A - アミノ酸ラセミ体の分割 - Google Patents

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Priority Applications (1)

Applications Claiming Priority (1)

Publications (2)

Family

ID=13231263

Family Applications (1)

Country Status (1)

Cited By (3)

Cited By (3)

Also Published As

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