CN102219706A - Method for preparing acetyl tyrosine ethyl ester monohydrate and product of acetyl tyrosine ethyl ester monohydrate - Google Patents
Method for preparing acetyl tyrosine ethyl ester monohydrate and product of acetyl tyrosine ethyl ester monohydrate Download PDFInfo
- Publication number
- CN102219706A CN102219706A CN2011101000378A CN201110100037A CN102219706A CN 102219706 A CN102219706 A CN 102219706A CN 2011101000378 A CN2011101000378 A CN 2011101000378A CN 201110100037 A CN201110100037 A CN 201110100037A CN 102219706 A CN102219706 A CN 102219706A
- Authority
- CN
- China
- Prior art keywords
- ethyl ester
- acetyl tyrosine
- reaction
- preparation
- ester monohydrate
- Prior art date
- 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.)
- Granted
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- -1 acetyl tyrosine ethyl ester monohydrate Chemical class 0.000 title claims abstract description 39
- 238000000034 method Methods 0.000 title abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 44
- 239000000243 solution Substances 0.000 claims abstract description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 24
- CAHKINHBCWCHCF-UHFFFAOYSA-N N-acetyltyrosine Chemical compound CC(=O)NC(C(O)=O)CC1=CC=C(O)C=C1 CAHKINHBCWCHCF-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000001816 cooling Methods 0.000 claims abstract description 16
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims abstract description 12
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims abstract description 12
- 239000011259 mixed solution Substances 0.000 claims abstract description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 12
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000001035 drying Methods 0.000 claims abstract description 11
- 238000005917 acylation reaction Methods 0.000 claims abstract description 10
- 239000012736 aqueous medium Substances 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims description 25
- 238000002425 crystallisation Methods 0.000 claims description 17
- 238000009413 insulation Methods 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 10
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 8
- 239000011707 mineral Substances 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 239000012141 concentrate Substances 0.000 claims description 6
- 238000010790 dilution Methods 0.000 claims description 6
- 239000012895 dilution Substances 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 6
- 238000013019 agitation Methods 0.000 claims description 5
- 238000005119 centrifugation Methods 0.000 claims description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
- 230000006837 decompression Effects 0.000 claims description 3
- 229910017604 nitric acid Inorganic materials 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 8
- 238000005265 energy consumption Methods 0.000 abstract description 3
- 230000007547 defect Effects 0.000 abstract 1
- 238000007865 diluting Methods 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 229940024606 amino acid Drugs 0.000 description 17
- 235000001014 amino acid Nutrition 0.000 description 17
- 239000000543 intermediate Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- 229960004756 ethanol Drugs 0.000 description 8
- 229960004441 tyrosine Drugs 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 150000001413 amino acids Chemical class 0.000 description 6
- 230000001105 regulatory effect Effects 0.000 description 6
- CAHKINHBCWCHCF-JTQLQIEISA-N N-acetyl-L-tyrosine Chemical compound CC(=O)N[C@H](C(O)=O)CC1=CC=C(O)C=C1 CAHKINHBCWCHCF-JTQLQIEISA-N 0.000 description 4
- 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 4
- 239000003814 drug Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229960001682 n-acetyltyrosine Drugs 0.000 description 4
- 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
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 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 2
- 108010064696 N,O-diacetylmuramidase Proteins 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000003064 anti-oxidating effect Effects 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 229960000935 dehydrated alcohol Drugs 0.000 description 2
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000003912 environmental pollution Methods 0.000 description 2
- 239000008396 flotation agent Substances 0.000 description 2
- 238000011031 large-scale manufacturing process Methods 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229940056360 penicillin g Drugs 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- SKAWDTAMLOJQNK-UHFFFAOYSA-N 2-acetamido-3-(4-hydroxyphenyl)propanoic acid ethyl ester Chemical compound CCOC(=O)C(NC(C)=O)CC1=CC=C(O)C=C1 SKAWDTAMLOJQNK-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 206010062717 Increased upper airway secretion Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229940093740 amino acid and derivative Drugs 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000003796 beauty Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- SKAWDTAMLOJQNK-LBPRGKRZSA-N ethyl N-acetyl-L-tyrosinate Chemical compound CCOC(=O)[C@@H](NC(C)=O)CC1=CC=C(O)C=C1 SKAWDTAMLOJQNK-LBPRGKRZSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 230000000050 nutritive effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 208000026435 phlegm Diseases 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 238000010094 polymer processing Methods 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007634 remodeling Methods 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 229940001516 sodium nitrate Drugs 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- REZQBEBOWJAQKS-UHFFFAOYSA-N triacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO REZQBEBOWJAQKS-UHFFFAOYSA-N 0.000 description 1
- ZNRSXPDDVNZGEN-UHFFFAOYSA-K trisodium;chloride;sulfate Chemical compound [Na+].[Na+].[Na+].[Cl-].[O-]S([O-])(=O)=O ZNRSXPDDVNZGEN-UHFFFAOYSA-K 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Description
Claims (7)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 201110100037 CN102219706B (en) | 2011-04-21 | 2011-04-21 | Method for preparing acetyl tyrosine ethyl ester monohydrate and product of acetyl tyrosine ethyl ester monohydrate |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 201110100037 CN102219706B (en) | 2011-04-21 | 2011-04-21 | Method for preparing acetyl tyrosine ethyl ester monohydrate and product of acetyl tyrosine ethyl ester monohydrate |
Publications (2)
Publication Number | Publication Date |
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CN102219706A true CN102219706A (en) | 2011-10-19 |
CN102219706B CN102219706B (en) | 2013-08-21 |
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CN 201110100037 Expired - Fee Related CN102219706B (en) | 2011-04-21 | 2011-04-21 | Method for preparing acetyl tyrosine ethyl ester monohydrate and product of acetyl tyrosine ethyl ester monohydrate |
Country Status (1)
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109530094A (en) * | 2019-01-17 | 2019-03-29 | 湖南中医药大学 | Amide groups hydroxycarboxylic acid/hydroximic acid compound and its application in mineral floating |
CN111153829A (en) * | 2019-12-26 | 2020-05-15 | 烟台鲁银药业有限公司 | Preparation method of N-acetyl-L-tyrosine |
CN111170883A (en) * | 2020-01-06 | 2020-05-19 | 岳阳科罗德联合化学工业有限公司 | Fatty acyl amino acid polyhydroxy ester compound and preparation method thereof |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9688611B2 (en) | 2015-10-21 | 2017-06-27 | King Fahd University Of Petroleum And Minerals | Synthesis of (S)-2-acetamido-3-(4-hydroxy-3-(3-methylbut-2-enyl) phenyl) propanoic acid derivatives |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5925363A (en) * | 1983-07-08 | 1984-02-09 | Torii Yakuhin Kk | Tyrosine derivative |
CN1594283A (en) * | 2004-06-24 | 2005-03-16 | 武汉武大弘元药业有限公司 | Process for preparing N-acetyl-L-tyrosine |
-
2011
- 2011-04-21 CN CN 201110100037 patent/CN102219706B/en not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5925363A (en) * | 1983-07-08 | 1984-02-09 | Torii Yakuhin Kk | Tyrosine derivative |
CN1594283A (en) * | 2004-06-24 | 2005-03-16 | 武汉武大弘元药业有限公司 | Process for preparing N-acetyl-L-tyrosine |
Non-Patent Citations (6)
Title |
---|
《Cryst.Struct.Comm》 19721231 A.F.Piert,F.Durant N-acetyl-L-tyrosine ethyl ester monohydrate:C13H17NO4•H2O 75-77 1-7 第1卷, 第2期 * |
A.F.PIERT,F.DURANT: "N-acetyl-L-tyrosine ethyl ester monohydrate:C13H17NO4•H2O", 《CRYST.STRUCT.COMM》, vol. 1, no. 2, 31 December 1972 (1972-12-31), pages 75 - 77 * |
宋霞等: "二氯亚砜-甲醇溶液中合成氨基酸甲酯盐酸盐的研究", 《化学试剂》, vol. 29, no. 11, 15 November 2007 (2007-11-15), pages 687 - 690 * |
尚岩等: "氨基酸酯合成方法最新研究进展", 《哈尔滨理工大学学报》, vol. 13, no. 02, 15 April 2008 (2008-04-15), pages 107 - 111 * |
思洋等: "氨基酸甲乙酯的合成及纯化", 《内蒙古医学院学报》, vol. 27, no. 01, 30 March 2005 (2005-03-30) * |
王炳琴,黎植昌: "氨基酸酯的制备方法及应用", 《氨基酸和生物资源》, vol. 17, no. 04, 30 December 1995 (1995-12-30), pages 40 - 45 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109530094A (en) * | 2019-01-17 | 2019-03-29 | 湖南中医药大学 | Amide groups hydroxycarboxylic acid/hydroximic acid compound and its application in mineral floating |
CN111153829A (en) * | 2019-12-26 | 2020-05-15 | 烟台鲁银药业有限公司 | Preparation method of N-acetyl-L-tyrosine |
CN111170883A (en) * | 2020-01-06 | 2020-05-19 | 岳阳科罗德联合化学工业有限公司 | Fatty acyl amino acid polyhydroxy ester compound and preparation method thereof |
Also Published As
Publication number | Publication date |
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CN102219706B (en) | 2013-08-21 |
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