NL8600132A - Werkwijze voor de bereiding van alfa-amino-alfa-waterstofcarbonzuuramiden. - Google Patents

Werkwijze voor de bereiding van alfa-amino-alfa-waterstofcarbonzuuramiden. Download PDF

Info

Publication number: NL8600132A
Authority: NL; Netherlands
Prior art keywords: amino; preparation; hydrogen peroxide; moles; alfa
Prior art date: 1986-01-22

Application number

NL8600132A

Other languages

English (en)

Dutch (nl)

Original Assignee

Stamicarbon

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.)

1986-01-22

Filing date

1986-01-22

Publication date

1987-08-17

1986-01-22 Application filed by Stamicarbon filed Critical Stamicarbon

1986-01-22 Priority to NL8600132A priority Critical patent/NL8600132A/nl

1986-12-15 Priority to EP86202259A priority patent/EP0232562B1/de

1986-12-15 Priority to ES86202259T priority patent/ES2020185B3/es

1986-12-15 Priority to DE8686202259T priority patent/DE3675922D1/de

1986-12-15 Priority to AT86202259T priority patent/ATE58720T1/de

1987-01-19 Priority to DK027787A priority patent/DK27787A/da

1987-01-20 Priority to IL81319A priority patent/IL81319A0/xx

1987-01-20 Priority to CA000527647A priority patent/CA1307001C/en

1987-01-21 Priority to BR8700251A priority patent/BR8700251A/pt

1987-01-22 Priority to JP62011507A priority patent/JPS62178556A/ja

1987-08-17 Publication of NL8600132A publication Critical patent/NL8600132A/nl

Links

238000000034 method Methods 0.000 title claims abstract description 18
238000002360 preparation method Methods 0.000 title claims abstract description 13
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 title 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 38
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 38
238000006243 chemical reaction Methods 0.000 claims abstract description 21
229910021529 ammonia Inorganic materials 0.000 claims abstract description 16
125000005219 aminonitrile group Chemical group 0.000 claims abstract description 10
125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 5
125000003118 aryl group Chemical group 0.000 claims abstract description 5
125000004404 heteroalkyl group Chemical group 0.000 claims abstract description 5
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 5
235000008206 alpha-amino acids Nutrition 0.000 claims description 11
150000001408 amides Chemical class 0.000 claims description 10
150000001370 alpha-amino acid derivatives Chemical class 0.000 claims description 8
125000000547 substituted alkyl group Chemical group 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 abstract description 4
YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 abstract 1
229960002163 hydrogen peroxide Drugs 0.000 description 14
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
-1 1-methylcyclohexyl Chemical group 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
150000002825 nitriles Chemical class 0.000 description 6
239000002253 acid Substances 0.000 description 5
150000003839 salts Chemical class 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
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
150000001371 alpha-amino acids Chemical class 0.000 description 3
235000001014 amino acid Nutrition 0.000 description 3
150000001413 amino acids Chemical class 0.000 description 3
239000002585 base Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
229910000069 nitrogen hydride Inorganic materials 0.000 description 3
230000003287 optical effect Effects 0.000 description 3
238000000926 separation method Methods 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
XDEHMKQLKPZERH-BYPYZUCNSA-N (2s)-2-amino-3-methylbutanamide Chemical compound CC(C)[C@H](N)C(N)=O XDEHMKQLKPZERH-BYPYZUCNSA-N 0.000 description 2
ZMMPZEFSSVTIIW-UHFFFAOYSA-N 2-amino-3-methylbutanenitrile Chemical compound CC(C)C(N)C#N ZMMPZEFSSVTIIW-UHFFFAOYSA-N 0.000 description 2
ROAHGHLLRAUFEQ-UHFFFAOYSA-N 2-amino-4-methylpentanenitrile Chemical group CC(C)CC(N)C#N ROAHGHLLRAUFEQ-UHFFFAOYSA-N 0.000 description 2
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
230000008901 benefit Effects 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
238000004821 distillation Methods 0.000 description 2
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000000203 mixture Substances 0.000 description 2
239000000243 solution Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
QCVCCWSPZIUXEA-SCSAIBSYSA-N (2s)-2-amino-3,3-dimethylbutanamide Chemical compound CC(C)(C)[C@H](N)C(N)=O QCVCCWSPZIUXEA-SCSAIBSYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
FJJYHTVHBVXEEQ-UHFFFAOYSA-N 2,2-dimethylpropanal Chemical compound CC(C)(C)C=O FJJYHTVHBVXEEQ-UHFFFAOYSA-N 0.000 description 1
108700023418 Amidases Proteins 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
150000007649 L alpha amino acids Chemical class 0.000 description 1
ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
241000589776 Pseudomonas putida Species 0.000 description 1
230000002411 adverse Effects 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
102000005922 amidase Human genes 0.000 description 1
AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 1
229960000723 ampicillin Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
235000019504 cigarettes Nutrition 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
238000006911 enzymatic reaction Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000001909 leucine group Chemical group [H]N(*)C(C(*)=O)C([H])([H])C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
125000000962 organic group Chemical group 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
238000011197 physicochemical method Methods 0.000 description 1
239000002243 precursor Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000758 substrate Substances 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/06—Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicinal Preparation (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Indole Compounds (AREA)

NL8600132A 1986-01-22 1986-01-22 Werkwijze voor de bereiding van alfa-amino-alfa-waterstofcarbonzuuramiden. NL8600132A (nl)

Priority Applications (10)

Application Number	Priority Date	Filing Date	Title
NL8600132A NL8600132A (nl)	1986-01-22	1986-01-22	Werkwijze voor de bereiding van alfa-amino-alfa-waterstofcarbonzuuramiden.
EP86202259A EP0232562B1 (de)	1986-01-22	1986-12-15	Verfahren zur Herstellung von alpha-Amino-alpha-Wasserstoff-Carbonsäureamiden
ES86202259T ES2020185B3 (es)	1986-01-22	1986-12-15	Proceso de preparacion de amidas de acido carboxilico alfa-amino alfa hidrogeno.
DE8686202259T DE3675922D1 (de)	1986-01-22	1986-12-15	Verfahren zur herstellung von alpha-amino-alpha-wasserstoff-carbonsaeureamiden.
AT86202259T ATE58720T1 (de)	1986-01-22	1986-12-15	Verfahren zur herstellung von alpha-amino-alphawasserstoff-carbons\|ureamiden.
DK027787A DK27787A (da)	1986-01-22	1987-01-19	Fremgangsmaade til fremstilling af alfa-amino-alfa-hydrogencarboxylsyreamider
IL81319A IL81319A0 (en)	1986-01-22	1987-01-20	Preparation of alpha-amino-alpha-hydrogen carboxylic acid amides
CA000527647A CA1307001C (en)	1986-01-22	1987-01-20	PROCESS FOR THE PREPARATION OF .alpha.-AMINO-.alpha.-HYDROGEN CARBOXYLIC ACID AMIDES
BR8700251A BR8700251A (pt)	1986-01-22	1987-01-21	Processo para a preparacao de amidas de acido alfa-amino-alfa-hidrogenio carboxilico
JP62011507A JPS62178556A (ja)	1986-01-22	1987-01-22	α−アミノ−α−水素カルボン酸アミドの製法

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
NL8600132A NL8600132A (nl)	1986-01-22	1986-01-22	Werkwijze voor de bereiding van alfa-amino-alfa-waterstofcarbonzuuramiden.
NL8600132		1986-01-22

Publications (1)

Publication Number	Publication Date
NL8600132A true NL8600132A (nl)	1987-08-17

Family

ID=19847450

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8600132A NL8600132A (nl)	1986-01-22	1986-01-22	Werkwijze voor de bereiding van alfa-amino-alfa-waterstofcarbonzuuramiden.

Country Status (10)

Country	Link
EP (1)	EP0232562B1 (de)
JP (1)	JPS62178556A (de)
AT (1)	ATE58720T1 (de)
BR (1)	BR8700251A (de)
CA (1)	CA1307001C (de)
DE (1)	DE3675922D1 (de)
DK (1)	DK27787A (de)
ES (1)	ES2020185B3 (de)
IL (1)	IL81319A0 (de)
NL (1)	NL8600132A (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2001163845A (ja) *	1999-12-13	2001-06-19	Mitsubishi Rayon Co Ltd	アミノ酸アミドの製造方法
JP2004099506A (ja) *	2002-09-09	2004-04-02	Mitsubishi Rayon Co Ltd	アミノ酸アミドの製造方法

1986
- 1986-01-22 NL NL8600132A patent/NL8600132A/nl not_active Application Discontinuation
- 1986-12-15 DE DE8686202259T patent/DE3675922D1/de not_active Expired - Lifetime
- 1986-12-15 EP EP86202259A patent/EP0232562B1/de not_active Expired - Lifetime
- 1986-12-15 AT AT86202259T patent/ATE58720T1/de not_active IP Right Cessation
- 1986-12-15 ES ES86202259T patent/ES2020185B3/es not_active Expired - Lifetime
1987
- 1987-01-19 DK DK027787A patent/DK27787A/da not_active Application Discontinuation
- 1987-01-20 CA CA000527647A patent/CA1307001C/en not_active Expired - Lifetime
- 1987-01-20 IL IL81319A patent/IL81319A0/xx unknown
- 1987-01-21 BR BR8700251A patent/BR8700251A/pt unknown
- 1987-01-22 JP JP62011507A patent/JPS62178556A/ja active Pending

Also Published As

Publication number	Publication date
EP0232562B1 (de)	1990-11-28
JPS62178556A (ja)	1987-08-05
BR8700251A (pt)	1987-12-01
DK27787D0 (da)	1987-01-19
EP0232562A1 (de)	1987-08-19
ES2020185B3 (es)	1991-08-01
CA1307001C (en)	1992-09-01
DK27787A (da)	1987-07-23
IL81319A0 (en)	1987-08-31
ATE58720T1 (de)	1990-12-15
DE3675922D1 (de)	1991-01-10

Legal Events

Date	Code	Title	Description
1987-08-17	A1B	A search report has been drawn up
1988-09-01	BV	The patent application has lapsed

Publication	Publication Date	Title
JPS6214543B2 (de)	1987-04-02
NL8600132A (nl)	1987-08-17	Werkwijze voor de bereiding van alfa-amino-alfa-waterstofcarbonzuuramiden.
US5276190A (en)	1994-01-04	Method for the preparation of an alcohol
NL8600131A (nl)	1987-08-17	Werkwijze voor de bereiding van alfa-amino-alfa-methylcarbonzuuramiden en alfa-amino-alfa-cycloalkylcarbonzuuramiden.
JP4395955B2 (ja)	2010-01-13	α−アミノ酸アミド類の製造法
FR2523576A1 (fr)	1983-09-23	Procede de preparation d'acides n-acyliminodiacetiques
US4551537A (en)	1985-11-05	Synthesis of alpha-aminonitriles
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BE1010768A3 (nl)	1999-01-05	Een werkwijze voor de bereiding van alpha-aminozuuramiden, alpha-aminozuren en derivaten ervan.
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