NO883381L - Fremgangsmaate ved fremstilling av n-((4-hydrosy-pyrrolidin-2-on-1-yl)-acetyl)-glycinamid. - Google Patents

Fremgangsmaate ved fremstilling av n-((4-hydrosy-pyrrolidin-2-on-1-yl)-acetyl)-glycinamid.

Info

Publication number: NO883381L
Authority: NO; Norway
Prior art keywords: acetyl; alkyl ester; glycine; pyrrolin; temperatures
Prior art date: 1987-07-30

Application number

NO88883381A

Other languages

English (en)

Norwegian (no)

Other versions

NO883381D0 (no

Inventor

Thomas Meul

Laurent Duc

Original Assignee

Lonza Ag

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.)

1987-07-30

Filing date

1988-07-29

Publication date

1989-01-31

1988-07-29 Application filed by Lonza Ag filed Critical Lonza Ag

1988-07-29 Publication of NO883381D0 publication Critical patent/NO883381D0/no

1989-01-31 Publication of NO883381L publication Critical patent/NO883381L/no

Links

238000000034 method Methods 0.000 title claims abstract description 15
238000002360 preparation method Methods 0.000 title description 4
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 21
238000006243 chemical reaction Methods 0.000 claims description 13
-1 4-hydroxy-pyrrolidin-2-on-1-yl Chemical group 0.000 claims description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
239000004471 Glycine Substances 0.000 claims description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 9
235000019445 benzyl alcohol Nutrition 0.000 claims description 7
239000000047 product Substances 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 5
125000005907 alkyl ester group Chemical group 0.000 claims description 5
229910021529 ammonia Inorganic materials 0.000 claims description 5
239000003054 catalyst Substances 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
229910052763 palladium Inorganic materials 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
239000012467 final product Substances 0.000 claims description 4
150000004678 hydrides Chemical class 0.000 claims description 4
230000001681 protective effect Effects 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 3
239000013067 intermediate product Substances 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
229910000033 sodium borohydride Inorganic materials 0.000 claims description 3
239000012279 sodium borohydride Substances 0.000 claims description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
239000003513 alkali Substances 0.000 claims description 2
229940098779 methanesulfonic acid Drugs 0.000 claims description 2
150000003512 tertiary amines Chemical class 0.000 claims description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
150000001408 amides Chemical class 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
239000000243 solution Substances 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
CVIXOOVAHSWDMO-UHFFFAOYSA-N 2-amino-N-[2-(4-hydroxy-2-oxopyrrolidin-1-yl)acetyl]acetamide Chemical compound OC1CC(N(C1)CC(=O)NC(CN)=O)=O CVIXOOVAHSWDMO-UHFFFAOYSA-N 0.000 description 3
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
238000007327 hydrogenolysis reaction Methods 0.000 description 2
238000002955 isolation Methods 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
JNYMRXDQVPIONI-HWKANZROSA-N methyl (e)-4-chloro-3-methoxybut-2-enoate Chemical compound COC(=O)\C=C(/CCl)OC JNYMRXDQVPIONI-HWKANZROSA-N 0.000 description 2
IHLAQQPQKRMGSS-UHFFFAOYSA-N oxiracetam Chemical compound NC(=O)CN1CC(O)CC1=O IHLAQQPQKRMGSS-UHFFFAOYSA-N 0.000 description 2
238000000746 purification Methods 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
238000010626 work up procedure Methods 0.000 description 2
TXTWXQXDMWILOF-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl)azanium;chloride Chemical compound [Cl-].CCOC(=O)C[NH3+] TXTWXQXDMWILOF-UHFFFAOYSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
BMOXYLBGPIDAAN-UHFFFAOYSA-N 2-(4-hydroxy-2-oxopyrrolidin-1-yl)acetic acid Chemical compound OC1CN(CC(O)=O)C(=O)C1 BMOXYLBGPIDAAN-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-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
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
230000009435 amidation Effects 0.000 description 1
238000007112 amidation reaction Methods 0.000 description 1
238000005349 anion exchange Methods 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000005341 cation exchange Methods 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
229960001227 oxiracetam Drugs 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Genetics & Genomics (AREA)
Biochemistry (AREA)
Biophysics (AREA)
General Health & Medical Sciences (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Molecular Biology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Life Sciences & Earth Sciences (AREA)
Pyrrole Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Peptides Or Proteins (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NO88883381A 1987-07-30 1988-07-29 Fremgangsmaate ved fremstilling av n-((4-hydrosy-pyrrolidin-2-on-1-yl)-acetyl)-glycinamid. NO883381L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH291987		1987-07-30

Publications (2)

Publication Number	Publication Date
NO883381D0 NO883381D0 (no)	1988-07-29
NO883381L true NO883381L (no)	1989-01-31

Family

ID=4244565

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO88883381A NO883381L (no)	1987-07-30	1988-07-29	Fremgangsmaate ved fremstilling av n-((4-hydrosy-pyrrolidin-2-on-1-yl)-acetyl)-glycinamid.

Country Status (6)

Country	Link
EP (1)	EP0301398A3 (fr)
JP (1)	JPS6450894A (fr)
DK (1)	DK356288A (fr)
HU (1)	HUT47597A (fr)
IL (1)	IL87216A0 (fr)
NO (1)	NO883381L (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH680293A5 (fr) *	1990-06-26	1992-07-31	Lonza Ag

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1190378B (it) *	1985-06-21	1988-02-16	Isf Spa	Derivati pirrolidonici
IL80071A0 (en) *	1985-09-24	1986-12-31	Lonza Ag	Pyrrolidine acetamide derivatives
HU195773B (en) *	1985-09-24	1988-07-28	Lonza Ag	Process for preparing alkyl esters of 4-alkoxy-3-pyrrolin-2-on-1-yl-acetic acid

1988
- 1988-06-28 DK DK356288A patent/DK356288A/da not_active Application Discontinuation
- 1988-07-20 EP EP88111706A patent/EP0301398A3/fr not_active Withdrawn
- 1988-07-26 JP JP63186669A patent/JPS6450894A/ja active Pending
- 1988-07-26 IL IL87216A patent/IL87216A0/xx unknown
- 1988-07-29 NO NO88883381A patent/NO883381L/no unknown
- 1988-07-29 HU HU884039A patent/HUT47597A/hu unknown

Also Published As

Publication number	Publication date
EP0301398A3 (fr)	1990-05-30
NO883381D0 (no)	1988-07-29
IL87216A0 (en)	1988-12-30
DK356288A (da)	1989-01-31
JPS6450894A (en)	1989-02-27
HUT47597A (en)	1989-03-28
EP0301398A2 (fr)	1989-02-01
DK356288D0 (da)	1988-06-28

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