NL7809121A - Optisch aktieve derivaten van mercapto-isoboterzuur. - Google Patents

Optisch aktieve derivaten van mercapto-isoboterzuur. Download PDF

Info

Publication number: NL7809121A
Authority: NL; Netherlands
Prior art keywords: residue; benzoyl; cinchonidine; mercapto; acid
Prior art date: 1978-09-07

Application number

NL7809121A

Other languages

English (en)

Dutch (nl)

Original Assignee

Oce Andeno B V Grubbenvorsterw

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.)

1978-09-07

Filing date

1978-09-07

Publication date

1980-03-11

1978-09-07 Application filed by Oce Andeno B V Grubbenvorsterw filed Critical Oce Andeno B V Grubbenvorsterw

1978-09-07 Priority to NL7809121A priority Critical patent/NL7809121A/nl

1979-08-31 Priority to EP79200477A priority patent/EP0008833B1/fr

1979-08-31 Priority to DE7979200477T priority patent/DE2961698D1/de

1979-09-04 Priority to US06/071,934 priority patent/US4585595A/en

1979-09-06 Priority to JP11468379A priority patent/JPS5538386A/ja

1980-03-11 Publication of NL7809121A publication Critical patent/NL7809121A/nl

Links

239000002253 acid Substances 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 19
KMPWYEUPVWOPIM-KODHJQJWSA-N cinchonidine Chemical compound C1=CC=C2C([C@H]([C@H]3[N@]4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-KODHJQJWSA-N 0.000 claims description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 15
KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 claims description 14
239000000203 mixture Substances 0.000 claims description 10
MHRDCHHESNJQIS-UHFFFAOYSA-N 2-methyl-3-sulfanylpropanoic acid Chemical compound SCC(C)C(O)=O MHRDCHHESNJQIS-UHFFFAOYSA-N 0.000 claims description 9
238000000034 method Methods 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 7
238000001953 recrystallisation Methods 0.000 claims description 7
238000006243 chemical reaction Methods 0.000 claims description 4
239000012043 crude product Substances 0.000 claims description 4
150000002148 esters Chemical class 0.000 claims description 4
239000000706 filtrate Substances 0.000 claims description 3
238000002844 melting Methods 0.000 claims description 3
230000008018 melting Effects 0.000 claims description 3
BCAYPPFBOJCRPN-UHFFFAOYSA-N 3-benzoylsulfanyl-2-methylpropanoic acid Chemical compound OC(=O)C(C)CSC(=O)C1=CC=CC=C1 BCAYPPFBOJCRPN-UHFFFAOYSA-N 0.000 claims description 2
238000005903 acid hydrolysis reaction Methods 0.000 claims description 2
-1 benzoyl compound Chemical class 0.000 claims description 2
239000007858 starting material Substances 0.000 claims description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 2
230000020176 deacylation Effects 0.000 claims 2
238000005947 deacylation reaction Methods 0.000 claims 2
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
238000005917 acylation reaction Methods 0.000 claims 1
235000019253 formic acid Nutrition 0.000 claims 1
238000010438 heat treatment Methods 0.000 claims 1
230000001681 protective effect Effects 0.000 claims 1
230000006340 racemization Effects 0.000 claims 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
238000003756 stirring Methods 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
238000009835 boiling 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
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
239000000047 product Substances 0.000 description 3
KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 3
238000010992 reflux Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-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
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
230000007017 scission Effects 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
UIQGEWJEWJMQSL-UHFFFAOYSA-N 2,2,4,4-tetramethylpentan-3-one Chemical compound CC(C)(C)C(=O)C(C)(C)C UIQGEWJEWJMQSL-UHFFFAOYSA-N 0.000 description 1
QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
JTMBCYAUSCBSEY-UHFFFAOYSA-N 2-methyl-2-sulfanylpropanoic acid Chemical class CC(C)(S)C(O)=O JTMBCYAUSCBSEY-UHFFFAOYSA-N 0.000 description 1
GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 description 1
238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
UIJGNTRUPZPVNG-UHFFFAOYSA-N benzenecarbothioic s-acid Chemical compound SC(=O)C1=CC=CC=C1 UIJGNTRUPZPVNG-UHFFFAOYSA-N 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
238000006480 benzoylation reaction Methods 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
230000006196 deacetylation Effects 0.000 description 1
238000003381 deacetylation reaction Methods 0.000 description 1
RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000010410 layer Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
229960002429 proline Drugs 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NL7809121A 1978-09-07 1978-09-07 Optisch aktieve derivaten van mercapto-isoboterzuur. NL7809121A (nl)

Priority Applications (5)

Application Number	Priority Date	Filing Date	Title
NL7809121A NL7809121A (nl)	1978-09-07	1978-09-07	Optisch aktieve derivaten van mercapto-isoboterzuur.
EP79200477A EP0008833B1 (fr)	1978-09-07	1979-08-31	Dérivés optiquement actifs de l'acide mercaptoisobutyrique et procédé pour leur préparation
DE7979200477T DE2961698D1 (en)	1978-09-07	1979-08-31	Optically active derivatives of mercaptoisobutyric acid and a process for preparing them
US06/071,934 US4585595A (en)	1978-09-07	1979-09-04	Optically active derivatives of mercaptoisobutyric acid and methods of preparation thereof
JP11468379A JPS5538386A (en)	1978-09-07	1979-09-06	Optically active derivative of mercaptoisobutyric acid

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
NL7809121		1978-09-07
NL7809121A NL7809121A (nl)	1978-09-07	1978-09-07	Optisch aktieve derivaten van mercapto-isoboterzuur.

Publications (1)

Publication Number	Publication Date
NL7809121A true NL7809121A (nl)	1980-03-11

Family

ID=19831497

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL7809121A NL7809121A (nl)	1978-09-07	1978-09-07	Optisch aktieve derivaten van mercapto-isoboterzuur.

Country Status (5)

Country	Link
US (1)	US4585595A (fr)
EP (1)	EP0008833B1 (fr)
JP (1)	JPS5538386A (fr)
DE (1)	DE2961698D1 (fr)
NL (1)	NL7809121A (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4559178A (en) *	1980-10-06	1985-12-17	American Home Products Corporation	Resolution of 3-benzoylthio-2-methyl-propanoic acid with (+)-dehydroabietylamine
IT1134458B (it) *	1980-11-26	1986-08-13	Real Sas Di Alberto Reiner	Derivato della n-acetil-cisteina ad attivita' terapeutica,procedimento per la sua preparazione e relative composizioni farmaceutiche
US4536601A (en) *	1982-09-28	1985-08-20	Dainippon Pharmaceutical Co., Ltd.	Optically active N-substituted phenylalaninols and use thereof
EP0130752B1 (fr) *	1983-07-04	1991-02-27	Mitsubishi Rayon Co., Ltd.	Procédé de préparation d'acides carboxyliques optiquement actifs et de leurs esters antipodes
JPH06740B2 (ja) *	1984-08-16	1994-01-05	三菱レイヨン株式会社	光学活性カルボン酸アミドの製造法
EP0259465A1 (fr) *	1986-03-07	1988-03-16	Wisconsin Alumni Research Foundation	Procede de preparation de derives de l'acide 3-acylthio-2-methylpropionic optiquement actifs
US5097043A (en) *	1988-01-15	1992-03-17	E. R. Squibb & Sons, Inc.	Process of preparing captopril
US5001251A (en) *	1988-01-15	1991-03-19	E. R. Squibb & Sons, Inc.	Optical resolution of DL-3-acylthio-2-methylpropanoic acid
US5543545A (en) *	1993-03-23	1996-08-06	Industrial Technology Research Institute	Method for the preparaton of α-methyl-β-acylthiopropionates
ES2061403B1 (es) *	1993-04-16	1995-06-16	Medichem Sa	Procedimiento de obtencion del acido d-(-) -3 acetiltio-2- metilpropionico.
CN109651218A (zh) *	2019-01-14	2019-04-19	浙江华海药业股份有限公司	一种制备s-(-)-苯甲酰巯基-2-甲基丙酸化合物的方法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2408095A (en) *	1943-11-11	1946-09-24	Du Pont	Highly useful compounds
GB1030389A (en) *	1964-08-20	1966-05-25	Beecham Group Ltd	Resolution of organic acid
US3636033A (en) *	1969-02-27	1972-01-18	Geigy Chem Corp	Addition product of an alpha beta-unsaturated ester and a thiocarboxylic acid
US4105776A (en) *	1976-06-21	1978-08-08	E. R. Squibb & Sons, Inc.	Proline derivatives and related compounds
AU509899B2 (en) *	1976-02-13	1980-05-29	E.R. Squibb & Sons, Inc.	Proline derivatives and related compounds
JPS54151912A (en) *	1978-05-18	1979-11-29	Santen Pharmaceutical Co Ltd	Manufacture of photoactive sulfur contained carboxylic acid

1978
- 1978-09-07 NL NL7809121A patent/NL7809121A/nl not_active Application Discontinuation
1979
- 1979-08-31 EP EP79200477A patent/EP0008833B1/fr not_active Expired
- 1979-08-31 DE DE7979200477T patent/DE2961698D1/de not_active Expired
- 1979-09-04 US US06/071,934 patent/US4585595A/en not_active Expired - Lifetime
- 1979-09-06 JP JP11468379A patent/JPS5538386A/ja active Granted

Also Published As

Publication number	Publication date
EP0008833B1 (fr)	1981-12-30
EP0008833A1 (fr)	1980-03-19
US4585595A (en)	1986-04-29
JPS6249268B2 (fr)	1987-10-19
JPS5538386A (en)	1980-03-17
DE2961698D1 (en)	1982-02-18

Legal Events

Date	Code	Title	Description
1982-05-03	BV	The patent application has lapsed

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