CA1331255C - Methode pour la production de chlorhydrate d'ester methyliques de l'-l-aspartyl-l-phenylalanine - Google Patents

Methode pour la production de chlorhydrate d'ester methyliques de l'-l-aspartyl-l-phenylalanine

Info

Publication number: CA1331255C
Authority: CA; Canada
Prior art keywords: alpha; aspartyl; aqueous medium; mol; amount
Prior art date: 1985-07-12
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 - Fee Related

Application number

CA 513597

Other languages

English (en)

Inventor

Katsumi Sugiyama

Toshihide Yukawa

Kiyo Adachi

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.)

Ajinomoto Co Inc

Original Assignee

Ajinomoto Co Inc

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.)

1985-07-12

Filing date

1986-07-11

Publication date

1994-08-02

1986-07-11 Application filed by Ajinomoto Co Inc filed Critical Ajinomoto Co Inc

1994-08-02 Application granted granted Critical

1994-08-02 Publication of CA1331255C publication Critical patent/CA1331255C/fr

2011-08-02 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 24
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 60
150000003841 chloride salts Chemical class 0.000 claims abstract description 25
229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 25
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 25
229910001504 inorganic chloride Inorganic materials 0.000 claims abstract description 24
239000013078 crystal Substances 0.000 claims abstract description 22
YZQCXOFQZKCETR-UHFFFAOYSA-N aspartyl-phenylalanine Chemical compound OC(=O)CC(N)C(=O)NC(C(O)=O)CC1=CC=CC=C1 YZQCXOFQZKCETR-UHFFFAOYSA-N 0.000 claims abstract 17
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 78
239000012736 aqueous medium Substances 0.000 claims description 40
238000001556 precipitation Methods 0.000 claims description 13
239000002609 medium Substances 0.000 claims description 3
238000006243 chemical reaction Methods 0.000 abstract description 10
229910052739 hydrogen Inorganic materials 0.000 abstract description 9
239000001257 hydrogen Substances 0.000 abstract description 9
230000003247 decreasing effect Effects 0.000 abstract description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract description 2
229910001507 metal halide Inorganic materials 0.000 abstract 1
150000005309 metal halides Chemical class 0.000 abstract 1
239000000203 mixture Substances 0.000 description 12
229960000443 hydrochloric acid Drugs 0.000 description 10
235000011167 hydrochloric acid Nutrition 0.000 description 10
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
150000003839 salts Chemical class 0.000 description 7
239000000243 solution Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
-1 hydrogen halides Chemical class 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 6
235000019270 ammonium chloride Nutrition 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
229910000039 hydrogen halide Inorganic materials 0.000 description 4
239000012433 hydrogen halide Substances 0.000 description 4
238000011835 investigation Methods 0.000 description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 description 3
229960005190 phenylalanine Drugs 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
239000012535 impurity Substances 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
238000004811 liquid chromatography Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
VSDUZFOSJDMAFZ-VIFPVBQESA-N methyl L-phenylalaninate Chemical compound COC(=O)[C@@H](N)CC1=CC=CC=C1 VSDUZFOSJDMAFZ-VIFPVBQESA-N 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
PNBMXFUTFSFLNU-BXRBKJIMSA-N (2s)-2-aminobutanedioic acid;(2s)-2-aminopropanoic acid Chemical class C[C@H](N)C(O)=O.OC(=O)[C@@H](N)CC(O)=O PNBMXFUTFSFLNU-BXRBKJIMSA-N 0.000 description 1
GWKOSRIHVSBBIA-REOHCLBHSA-N (3s)-3-aminooxolane-2,5-dione Chemical compound N[C@H]1CC(=O)OC1=O GWKOSRIHVSBBIA-REOHCLBHSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical class N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
241001077660 Molo Species 0.000 description 1
206010067482 No adverse event Diseases 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
238000007259 addition reaction Methods 0.000 description 1
230000002411 adverse Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
CKLJMWTZIZZHCS-REOHCLBHSA-N aspartic acid group Chemical group N[C@@H](CC(=O)O)C(=O)O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
235000011116 calcium hydroxide Nutrition 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229910017053 inorganic salt Inorganic materials 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910001510 metal chloride Inorganic materials 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
150000004692 metal hydroxides Chemical class 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
229910021511 zinc hydroxide Inorganic materials 0.000 description 1

Landscapes

Peptides Or Proteins (AREA)

CA 513597 1985-07-12 1986-07-11 Methode pour la production de chlorhydrate d'ester methyliques de l'-l-aspartyl-l-phenylalanine Expired - Fee Related CA1331255C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP15364585A JPH07640B2 (ja)	1985-07-12	1985-07-12	α−Ｌ−アスパルチル−Ｌ−フエニルアラニンメチルエステル塩酸塩の製造法
JP153645/1985		1985-07-12

Publications (1)

Publication Number	Publication Date
CA1331255C true CA1331255C (fr)	1994-08-02

Family

ID=15567058

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 513597 Expired - Fee Related CA1331255C (fr)	1985-07-12	1986-07-11	Methode pour la production de chlorhydrate d'ester methyliques de l'-l-aspartyl-l-phenylalanine

Country Status (2)

Country	Link
JP (1)	JPH07640B2 (fr)
CA (1)	CA1331255C (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0489479A (ja) *	1990-08-01	1992-03-23	Ajinomoto Co Inc	光学活性トリプトファンの回収方法

1985
- 1985-07-12 JP JP15364585A patent/JPH07640B2/ja not_active Expired - Lifetime
1986
- 1986-07-11 CA CA 513597 patent/CA1331255C/fr not_active Expired - Fee Related

Also Published As

Publication number	Publication date
JPH07640B2 (ja)	1995-01-11
JPS6216498A (ja)	1987-01-24

Publication	Publication Date	Title
EP0127411B1 (fr)	1988-08-10	Procédé pour la fabrication d'ester méthyle d'alpha-L-aspartyl-L-phénylalanine et son chlorhydrate
JPS5836399A (ja)	1983-03-03	ヒトインシユリン誘導体の製造方法
JPS60164495A (ja)	1985-08-27	Ｎ‐ホルミルアミノ酸とペプチド残基の酵素的結合法
CA1331255C (fr)	1994-08-02	Methode pour la production de chlorhydrate d'ester methyliques de l'-l-aspartyl-l-phenylalanine
US5554791A (en)	1996-09-10	Process for producing [S,S]-ethylenediamine-N,N'-disuccinic acid
US4618695A (en)	1986-10-21	Method of preparing methyl ester and its hydrochloride
US5225587A (en)	1993-07-06	Method of producing α-L-aspartyl-L-phenylalanine methyl ester hydrochloride
JP2002047258A (ja)	2002-02-12	Ｎ−イソプロピルグリシンの製造方法
US5304671A (en)	1994-04-19	Method for recovery of α-L-aspartyl-L-phenylalanine methyl ester, L-phenylalanine and L-aspartic acid
US4962231A (en)	1990-10-09	Preparation of D- or L-alanine or high enantiomeric purity
EP0327030B1 (fr)	1995-01-25	Méthode pour produire des dérivés de l'alpha-aspartyl-phénylalanine
CA2166246A1 (fr)	1996-06-29	Methode de preparation de derives d'amide d'.alpha.-l-aspartyldipeptide
US4673744A (en)	1987-06-16	Method for conversion of β-aspartylphenylalanine derivatives to .alpha.
KR930008088B1 (ko)	1993-08-25	N-보호된-L-α-아스파틸-L-페닐알라닌의 제조방법
US5581009A (en)	1996-12-03	Process for crystallization of L-phenylalanine monomethyl sulfate using added salt
JP2513159B2 (ja)	1996-07-03	Ｎ−ホルミル−Ｌ−α−アスパルチル−Ｌ−フェニルアラニンの製法
JPH0696595B2 (ja)	1994-11-30	Ｎ−保護−Ｌ−α−アスパルチル−Ｌ−フエニルアラニンの製法
JP2513155B2 (ja)	1996-07-03	Ｎ−保護−Ｌ−α−アスパルチル−Ｌ−フェニルアラニンの製法
EP0151651B1 (fr)	1988-10-05	Procédé pour la préparation d'un produit de départ pour la production de la phénylalanine
JP2896259B2 (ja)	1999-05-31	フェニルアラニンの単離方法
GB1587680A (en)	1981-04-08	Process for n-acylating amino acids
KR880000038B1 (ko)	1988-02-20	α-L-아스파틸-L-페닐알라닌 메틸 에스테르의 정제방법
JPS5944346A (ja)	1984-03-12	セリンの製造法
JPS61293955A (ja)	1986-12-24	アミノ酸の製造方法
JPS5852252A (ja)	1983-03-28	ジペプチドエステルとアミノ酸エステルとの付加化合物の分解法

Legal Events

Date	Code	Title	Description
2003-08-04	MKLA	Lapsed

CA1331255C - Methode pour la production de chlorhydrate d'ester methyliques de l'-l-aspartyl-l-phenylalanine - Google Patents