CA1120877A - N-acetylation selective d'acides amines par conversion avec un cetene en solution aqueuse - Google Patents

N-acetylation selective d'acides amines par conversion avec un cetene en solution aqueuse

Info

Publication number: CA1120877A
Authority: CA; Canada
Prior art keywords: amino acid; solution; amino acids; process according; value
Prior art date: 1977-09-13
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.): Expired

Application number

CA000311172A

Other languages

English (en)

Inventor

Giselher Franzmann

Hans-Leo Hulsmann

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.)

Dynamit Nobel AG

Original Assignee

Dynamit Nobel 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.)

1977-09-13

Filing date

1978-09-12

Publication date

1982-03-30

1978-09-12 Application filed by Dynamit Nobel AG filed Critical Dynamit Nobel AG

1982-03-30 Application granted granted Critical

1982-03-30 Publication of CA1120877A publication Critical patent/CA1120877A/fr

Status Expired legal-status Critical Current

Links

150000001413 amino acids Chemical class 0.000 title claims abstract description 38
238000006243 chemical reaction Methods 0.000 title claims abstract description 28
239000007864 aqueous solution Substances 0.000 title claims abstract description 9
150000002561 ketenes Chemical class 0.000 title claims abstract description 6
239000000243 solution Substances 0.000 claims abstract description 57
CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 claims abstract description 20
238000000034 method Methods 0.000 claims abstract description 18
-1 N-acetyl-amino Chemical group 0.000 claims abstract description 10
239000003513 alkali Substances 0.000 claims abstract description 10
230000002255 enzymatic effect Effects 0.000 claims abstract description 5
230000007062 hydrolysis Effects 0.000 claims abstract description 3
238000006460 hydrolysis reaction Methods 0.000 claims abstract description 3
230000003287 optical effect Effects 0.000 claims abstract description 3
229940024606 amino acid Drugs 0.000 claims description 40
COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Chemical compound OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 3
QIVBCDIJIAJPQS-UHFFFAOYSA-N tryptophan Chemical compound C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims description 3
238000009835 boiling Methods 0.000 claims description 2
238000007710 freezing Methods 0.000 claims description 2
230000008014 freezing Effects 0.000 claims description 2
FFEARJCKVFRZRR-UHFFFAOYSA-N L-Methionine Natural products CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 claims 1
FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims 1
229930195722 L-methionine Natural products 0.000 claims 1
229960004452 methionine Drugs 0.000 claims 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
235000011121 sodium hydroxide Nutrition 0.000 description 11
COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 10
239000000047 product Substances 0.000 description 7
229960005190 phenylalanine Drugs 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
238000000746 purification Methods 0.000 description 3
238000000926 separation method Methods 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
ZGUNAGUHMKGQNY-SSDOTTSWSA-N D-alpha-phenylglycine Chemical compound OC(=O)[C@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-SSDOTTSWSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-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
239000003153 chemical reaction reagent Substances 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
239000000758 substrate Substances 0.000 description 2
229960004799 tryptophan Drugs 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
BYNFPGLZQXITMV-VWURTLBMSA-N (2s)-2-amino-3-phenylpropanoic acid;(2s)-2-aminopropanoic acid Chemical compound C[C@H](N)C(O)=O.OC(=O)[C@@H](N)CC1=CC=CC=C1 BYNFPGLZQXITMV-VWURTLBMSA-N 0.000 description 1
VKDFZMMOLPIWQQ-UHFFFAOYSA-N 2-acetamido-2-phenylacetic acid Chemical compound CC(=O)NC(C(O)=O)C1=CC=CC=C1 VKDFZMMOLPIWQQ-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
150000008575 L-amino acids Chemical class 0.000 description 1
125000003047 N-acetyl group Chemical group 0.000 description 1
CBQJSKKFNMDLON-JTQLQIEISA-M N-acetyl-L-phenylalaninate Chemical compound CC(=O)N[C@H](C([O-])=O)CC1=CC=CC=C1 CBQJSKKFNMDLON-JTQLQIEISA-M 0.000 description 1
JJIHLJJYMXLCOY-BYPYZUCNSA-N N-acetyl-L-serine Chemical compound CC(=O)N[C@@H](CO)C(O)=O JJIHLJJYMXLCOY-BYPYZUCNSA-N 0.000 description 1
CBQJSKKFNMDLON-UHFFFAOYSA-N N-acetylphenylalanine Chemical compound CC(=O)NC(C(O)=O)CC1=CC=CC=C1 CBQJSKKFNMDLON-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
239000006035 Tryptophane Substances 0.000 description 1
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
ZGUNAGUHMKGQNY-UHFFFAOYSA-N alpha-phenylglycine Chemical compound OC(=O)C(N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-UHFFFAOYSA-N 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
239000008366 buffered solution Substances 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
238000010979 pH adjustment Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
MTCFGRXMJLQNBG-UHFFFAOYSA-N serine Chemical compound OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/20—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals substituted additionally by nitrogen atoms, e.g. tryptophane

Landscapes

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

CA000311172A 1977-09-13 1978-09-12 N-acetylation selective d'acides amines par conversion avec un cetene en solution aqueuse Expired CA1120877A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19772741081 DE2741081A1 (de)	1977-09-13	1977-09-13	Verfahren zur vollstaendigen, selektiven n-acetylierung von aminosaeuren durch umsetzung mit keten in waessriger loesung
DEP2741081.7		1977-09-13

Publications (1)

Publication Number	Publication Date
CA1120877A true CA1120877A (fr)	1982-03-30

Family

ID=6018776

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000311172A Expired CA1120877A (fr)	1977-09-13	1978-09-12	N-acetylation selective d'acides amines par conversion avec un cetene en solution aqueuse

Country Status (8)

Country	Link
JP (1)	JPS5448712A (fr)
BE (1)	BE870441A (fr)
CA (1)	CA1120877A (fr)
DE (1)	DE2741081A1 (fr)
FR (1)	FR2402645A1 (fr)
GB (1)	GB1587680A (fr)
IT (1)	IT1106908B (fr)
NL (1)	NL7809296A (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2740380A1 (de) *	1977-09-08	1979-03-15	Dynamit Nobel Ag	Verfahren zur racemisierung optisch aktiver n-acyl-aminosaeuren in waessriger loesung
DE3318933C1 (de) *	1983-05-25	1984-06-07	Degussa Ag, 6000 Frankfurt	Verfahren zur Trennung von L-Leucin und L-Isoleucin
HU190864B (en) *	1983-12-08	1986-11-28	Alkaloida Vegyeszeti Gyar	Process for production of phenil-alanin derivatives

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
YU35105B (en) *	1972-04-24	1980-09-25	Krka Tovarna Zdravil	Process for preparing acetylamine derivatives of 2,4,6-triiodo-benzoic acid

1977
- 1977-09-13 DE DE19772741081 patent/DE2741081A1/de not_active Withdrawn
1978
- 1978-05-26 GB GB23497/78A patent/GB1587680A/en not_active Expired
- 1978-08-29 FR FR7824934A patent/FR2402645A1/fr not_active Withdrawn
- 1978-09-11 JP JP11159978A patent/JPS5448712A/ja active Pending
- 1978-09-12 IT IT51061/78A patent/IT1106908B/it active
- 1978-09-12 CA CA000311172A patent/CA1120877A/fr not_active Expired
- 1978-09-12 NL NL7809296A patent/NL7809296A/xx not_active Application Discontinuation
- 1978-09-13 BE BE190451A patent/BE870441A/fr unknown

Also Published As

Publication number	Publication date
IT1106908B (it)	1985-11-18
NL7809296A (nl)	1979-03-15
JPS5448712A (en)	1979-04-17
IT7851061A0 (it)	1978-09-12
DE2741081A1 (de)	1979-03-22
BE870441A (fr)	1979-01-02
GB1587680A (en)	1981-04-08
FR2402645A1 (fr)	1979-04-06

Legal Events

Date	Code	Title	Description
1999-03-30	MKEX	Expiry

Publication	Publication Date	Title
CA1052716A (fr)	1979-04-17	Procede de resolution enzymatique du dl-phenyl-glycine-amide
US2511867A (en)	1950-06-20	Method fob separating enantiomers
CA1120877A (fr)	1982-03-30	N-acetylation selective d'acides amines par conversion avec un cetene en solution aqueuse
JP3694921B2 (ja)	2005-09-14	バリンの精製法
US3386888A (en)	1968-06-04	Resolution of racemic amino acids
JPS6354346A (ja)	1988-03-08	光学活性フェニルアラニンのラセミ化方法
JPH0789914A (ja)	1995-04-04	オルニチンと酸性アミノ酸類又はケト酸類との塩の製造法
KR900001610B1 (ko)	1990-03-17	L-시스테인 염산염의 1수화물의 분리방법
JP3528205B2 (ja)	2004-05-17	Ｌ−３，４−ジヒドロキシフェニルアラニンの製造方法
CA1117142A (fr)	1982-01-26	Procede de racemisation d'acides n-acyl-amines optiquement actifs en solution dans l'eau
US3669837A (en)	1972-06-13	Process for producing 3-(3,4-dimethoxyphenyl)l-alanine by resolution
CA1303628C (fr)	1992-06-16	Methode pour la racemisation de serine optiquement active
Benoiton et al.	1965	AN IMPROVED SYNTHESIS OF ϵ-N-ACETYL-l-LYSINE AND SIMILAR COMPOUNDS
JP4548756B2 (ja)	2010-09-22	アミノ酸アミドの精製法
JPS6231915B2 (fr)	1987-07-10
JP2505487B2 (ja)	1996-06-12	光学活性リジンのラセミ化法
NO149779B (no)	1984-03-12	Fremgangsmaate for fremstilling av d-(-)-fenylgycinforbindelser ved enzymatisk hydantoinhydrolyse
DE59607329D1 (de)	2001-08-23	Verfahren zur herstellung von n-acetyl-d,l-alpha-aminocarbonsäuren
JPS6224076B2 (fr)	1987-05-26
JPH0665657B2 (ja)	1994-08-24	光学活性マンデル酸の製法
JPH0267256A (ja)	1990-03-07	カルニチンおよびカルニチンニトリルの単離精製法
IL95038A (en)	1995-10-31	Preparation of d-histidine and derivatives thereof by asymmetric transformation of l-histidine
JPH0825972B2 (ja)	1996-03-13	アスパラギン酸の精製法
SU594106A1 (ru)	1978-02-25	Способ получени рацематов кислых аминокислот
CN106632398A (zh)	2017-05-10	一种头孢替安酯的制备方法