CAS: 15028-39-4; (S)-Methyl 2-Amino-2-Phenylacetate Hydrochloride

该化合物是一种以其特定的立体化学和功能组为特征的手性氨基酸衍生物,其特征是附于甘油主干柱的甲型碳的一个联苯组,这有利于其芳香特性.甲基酯功能组与其自由酸形式相比,其脂性会增强,使其在有机溶剂中更易溶于.作为盐盐,它显示出水溶液的稳定性和溶性会提高,这对药物和生物化学的各种应用有利.这种化合物经常被用于不对称合成,并且作为制作生物活性分子的建筑块.其性能在药物开发中具有显著意义,因为(S)抗生素的特性可能表现出与(R)对应方不同的生物活动.

结构式图片

相似化合物

19883-41-1 15028-40-7 37760-98-8

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合成工艺路线路线简述

    [(S)-1-(4-Methoxy-Phenyl)-Ethyl]-[1-Phenyl-Meth-(E)-Ylidene]-Amine置于盐酸,Ammonium Cerium(Iv) Nitrate,Lithium Perchlorate体系中,用 水,乙腈 用作溶剂,化学反应 4.0H,反应生成(S)-(+)-2-苯甘氨酸甲酯 盐酸盐
    参考文献:醛亚胺中的三甲基甲硅烷基氰化物及其在合成(S)-苯基甘氨酸甲酯中的应用
    标题:醛亚胺中的三甲基甲硅烷基氰化物及其在合成(S)-苯基甘氨酸甲酯中的应用
    摘要:研发了在乙腈中存在liclo 4或bf 3 .et 2 O的情况下,向各种芳基醛亚胺中添加tmscn(斯特雷克反应).该反应以非常高的收率提供了加成产物.该方法已成功地用于合成(S)-苯基甘氨酸甲酯.
    Doi:10.1016/j.Tetlet.2004.11.015

    海关参考信息

    专利信息


    专利号:EP-2173892-B8
    优先权日:2007-07-27
    标题:Process for the preparation of immobilised recombinant Penicillin Acylase biocatalyst from Achromobacter sp CCM 4824 expressed in E. coli BL21 CCM 7394 and its use for the synthesis of beta-lactam antiobiotics
    发明人:DATLA ANUPAMA; RAJASEKAR VYASARAYANI WILLIAMS; KYSLIK PAVEL; BECKA STANISLAV; KRISHNAKANT ASHAR TRUPTI; YOGESH ZAMBRE SUJATA; NIKUNJ KUMAR
    权利人:FERMENTA BIOTECH LTD
    摘要:The present invention discloses isolation of Penicillin Acylase (PA) from Achromobacter sp CCM 4824 expressed in recombinant strain E. coli BL21 CCM 7394 bearing the recombinant plasmid pKXIP1 and processing of PA into biocatalyst useful for the industrial synthesis of antibiotics. More particularly the invention discloses a synthesis of semi-synthetic β-lactam antibiotics in the reaction mixture consisting of activated acyl-donor (D-p-hydroxyphenylglycine methyl ester or amide for Amoxicillin and Cefadroxil; D-phenylglycine methyl ester or amide for Ampicillin and Cephalexin) and nucleophile (6-APA or 7-ADCA) catalyzed by PA obtained from recombinant E. coli BL21 CCM 7394 as the biocatalyst.

    专利号:US-2018312463-A1
    优先权日:2015-10-22
    标题:Synthesis of Cyclohexane Carboxamide Derivatives Useful as Sensates in Consumer Products
    发明人:YELM KENNETH EDWARD; WOS JOHN AUGUST; BUNKE GREGORY MARK; FREDERICK HEATH; HAUGHT JOHN CHRISTIAN; HOKE STEVEN HAMILTON; SREEKRISHNA KOTI TATACHAR; LIN YAKANG
    权利人:PROCTER & GAMBLE
    摘要:Synthesis methods to produce a series of carboxamides built off of an (S)-2-amino acid backbone or an (R)-2-amino acid backbone, depending upon the desired diastereomer of the end product.

    专利号:US-6218138-B1
    优先权日:1998-05-26
    标 题 :Synthesis of beta-lactam antibiotics with immobilized penicillin amidase
    发明人:ILHAN FERHAT; KRAEMER DIETER
    权利人:UNIFAR KIMYA SANAYI VE TICARET
    摘要:Beta-lactam antibiotics are synthesized by reacting an amino-beta-lactam component with a corresponding amino-group-containing acylating side-chain component in the presence of penicillin amidase from E. coli covalently immobilized on support particles. The resulting beta-lactam antibiotic product is solubilized by adding an acid such as sulfuric acid to lower the pH to 1.0 at a temperature in the range of 0° C. to +5° C. The immobilized penicillin amidase is substantially inactivated by the acid. After separating the beta-lactam antibiotic product, the immobilized penicillin amidase is substantially reactivated for reuse in antibiotic synthesis by treatment with a buffer having about a neutral pH. Antibiotics that can be produced include ampicillin, amoxicillin, cephalexin, cefaclor and cefadroxil. Support particles that can be used include particles having a macroporous structure and a particle diameter of 10-1000 mum, particles having oxirane groups, particles made of a synthetic polymer and inorganic particles such as porous glass particles.

    专利号:US-6515126-B2
    优先权日:2000-02-28
    标 题:Chemical synthesis of spirocyclic piperidines by double ring-closing metathesis
    发明人:ASHWOOD MICHAEL STEWART; COTTRELL IAN FRANK; COWDEN CAMERON JOHN; WALLACE DEBRA JANE
    权利人:MERCK SHARP & DOHME
    摘要:The present invention relates to a process for the preparation of a compound of formula (I) n wherein Ts is a tosylate group and R is an alkyl group, an unsubstituted phenyl or substituted phenyl ring, or a benzyl or substituted benzyl group; which comprises: n (i) cyclising a compound of formula (II) n in the presence of a suitable catalyst; and n (ii) purifying and collecting the resultant compound of formula (I).

    专利号:EP-0946499-B1
    优先权日:1996-11-22
    标 题 :N-(aryl/heteroaryl/alkylacetyl) amino acid amides, pharmaceutical compositions comprising same, and methods for inhibiting beta-amyloid peptide release and/or its synthesis by use of such compounds
    发明人:WU JING; TUNG JAY S; NISSEN JEFFREY S; MABRY THOMAS E; LATIMER LEE H; EID CLARK NORMAN; AUDIA JAMES E
    权利人:ELAN PHARM INC; LILLY CO ELI
    摘要:Disclosed are compounds which inhibit beta -amyloid peptide release and/or its synthesis, and, accordingly, have utility in treating Alzheimer's disease. Also disclosed are pharmaceutical compositions comprising a compound which inhibits beta -amyloid peptide release and/or its synthesis as well as methods for treating Alzheimer's disease both prophylactically and therapeutically with such pharmaceutical compositions. Said compounds are represented by formula (I), wherein R<1> is selected from the group consisting of: a) alkyl, alkenyl, alkaryl, alkcycloalkyl, aryl, cycloalkyl, cycloalkenyl, heteroaryl and heterocyclic; b) a substituted phenyl group of formula (II), wherein R is alkylene of from 1 to 8 carbon atoms, m is an integer equal to 0 or 1, and c) 1- or 2-naphthyl substituted at the 5, 6, 7 and/or 8 positions, R<2> is selected from the group consisting of hydrogen, alkyl of from 1 to 4 carbon atoms, alkylalkoxy of from 1 to 4 carbon atoms, alkylthioalkoxy of from 1 to 4 carbon atoms; and R<3> and R<3'> are independently selected from the group consisting of: (a) hydrogen, (b) alkyl, (c) -(R<7>)n(W)p, wherein R<7> is an alkylene group, W is selected from the group consisting of (i) formula (A); (ii) heteroaryl; and (iii) N-heterocyclic, and n is an integer equal to 0 or 1, and p is an integer equal to 1 to 3; (d) -CH( phi )CH2C(O)O-Q where Q is selected from the group consisting of alkyl, aryl, heteroaryl and heterocyclic; X' is hydrogen, hydroxy or fluoro; X'' is hydrogen, hydroxy or fluoro, or X' and X'' together form an oxo group, Z is selected from the group consisting of a bond covalently linking R<1> to -CX'X''-, oxygen and sulfur.

    专利号:US-6849650-B2
    优先权日:1998-02-27
    标 题:Heterocyclic compounds, pharmaceutical compositions comprising same, and methods for inhibiting β-amyloid peptide release and/or its synthesis by use of such compounds
    发明人:THORSETT EUGENE D; PORTER WARREN J; NISSEN JEFFREY S; LATIMER LEE H; AUDIA JAMES E; DROSTE JAMES
    权利人:ATHENA NEUROSCIENCES INC; LILLY CO ELI
    摘要:Disclosed are compounds which inhibit β-amyloid peptide release and/or its synthesis, and, accordingly, have utility in treating Alzheimer's disease. Also disclosed are pharmaceutical compositions comprising a compound which inhibits β-amyloid peptide release and/or its synthesis as well as methods for treating Alzheimer's disease both prophylactically and therapeutically with such pharmaceutical compositions.
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    主要参考文献

    [参考文献]: Luckose F, Et Al. Effects Of Amino Acid Derivatives On Physical, Mental, And Physiological Activities. Crit Rev Food Sci Nutr. 2015;55(13):1793-1144.

    合成参考文献


    参考文献:10.1134/s1070428013060080
    摘要:Ran D, Shen T, Zhou X, Li J, Cui F, Ma C, Song Q. Asymmetric henry reaction catalyzed by chiral schiff base. Russian Journal of Organic Chemistry. 2013 Jun;49(6):849–52. doi: 10.1134/s1070428013060080.
    参考文献:10.1007/s00044-012-0399-x
    摘要:Trejo Muñoz CR, Mancilla Percino T, Mera Jiménez E, Correa-Basurto J, Trujillo Ferrara JG. Partition coefficient determination of a series of isoindolines-2-substituted and its correlation with their antiproliferative activity on HeLa cells. Medicinal Chemistry Research. 2012 Dec 20;22(8):4039–45. doi: 10.1007/s00044-012-0399-x.
    参考文献:10.1007/s10570-019-02752-y
    摘要:Wang J, Wan J, Ma Y, Wang Y. Macroscopic and microscopic properties of fibers after enzymatic deinking of mixed office waste paper. Cellulose. 2019 Sep 13;26(18):9863–75. doi: 10.1007/s10570-019-02752-y.
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