[(3-乙氧基-1-甲基-3-氧代丙-1-烯基)氨基](4-羟基苯基)乙酸钾 | 57938-86-0

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 甘氨酸类衍生物
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: [(3-乙氧基-1-甲基-3-氧代丙-1-烯基)氨基](4-羟基苯基)乙酸钾
• 中文别名: [(3-乙氧基-1-甲基-3-羰基丙-1-烯基)氨基](4-羟基苯基)乙酸钾
• 英文名称: Dane salt of racemic p-hydroxyphenylglycine
• 英文别名: N-[2-ethoxycarbonyl-1-methylvinyl]α-amino-(4-hydoxyphenyl)acetic acid potassium salt；potassium-D-N-(2-ethoxycarbonyl-1-methyl-vinyl)-α-amino-(p-hydroxy-phenyl)-acetate；Potassium ((3-ethoxy-1-methyl-3-oxoprop-1-enyl)amino)(4-hydroxyphenyl)acetate；potassium;2-[[(E)-4-ethoxy-4-oxobut-2-en-2-yl]amino]-2-(4-hydroxyphenyl)acetate
• CAS: 57938-86-0；83918-72-3
• 化学式: C₁₄H₁₆NO₅*K
• 分子量: 317.383
• InChiKey: KCIVNTJLAYJMEK-HRNDJLQDSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.76
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  98.7
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 海关编码：
  2922509090

反应信息

• 作为反应物：
  描述：

  7-氨基-3-甲基-8-氧代-5-硫杂-1-氮杂双环[4.2.0]辛-2-烯-2-甲酸 、 2,7-二羟基萘 、 三甲基乙酰氯 、 [(3-乙氧基-1-甲基-3-氧代丙-1-烯基)氨基](4-羟基苯基)乙酸钾 以60%的产率得到cefadroxil/2,7-dihydroxynaphthalene complex
  参考文献：
  名称：

  使用包合诱导的不对称转化通过偶联 β-内酰胺核和外消旋氨基酸侧链合成头孢菌素类抗生素

  摘要：

  头孢菌素类抗生素头孢氨苄、头孢拉定和头孢羟氨苄是通过将它们的β-内酰胺核和外消旋氨基酸侧链前体偶联而成的。最初获得的头孢菌素差向异构体混合物经过包合诱导的不对称转化，导致表头孢菌素差向异构化为具有正确非对映体构型的头孢菌素。

  DOI：

  10.1002/1099-0690(200105)2001:10<1817::aid-ejoc1817>3.0.co;2-c
• 作为产物：
  描述：

  N-(4-羟苯基)甘氨酸 在 氢氧化钾 、 溶剂黄146 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 生成 [(3-乙氧基-1-甲基-3-氧代丙-1-烯基)氨基](4-羟基苯基)乙酸钾
  参考文献：
  名称：

  Process for preparing alpha-amino-phenylacetic acid-trifluoromethane

  摘要：

  揭示了一种制备化合物的过程，化合物的化学式为(VI) ##STR1## 其中X为氢原子或OH，Y为氢原子、OH或甲基基团，R.sup.2为CH--COOR基团或化学式(XI) ##STR2## 中的基团，R为C.sub.1至C.sub.2烷基基团，包括以下步骤：将化学式(IV)的缩合盐与三氟甲烷磺酸的活性衍生物反应。化合物的化学式(VI)是制备具有抗生素活性的青霉素和头孢菌素的中间体。

  公开号：

  US05338868A1

文献信息

• Process for preparation of 7-[alpha-amino (4-hydroxyphenyl) acetamido]-3-substituted-3-cephem-4-carboxylic acid
  申请人：Tyagi Dutt Om

  公开号：US20050113570A1

  公开（公告）日：2005-05-26

  A process for preparation of 7-[D-α-amino-α-(4-hydroxyphenyl)acetamido]-3-(1-propen-1-yl)-3-cephem-4-carboxylic acid viz. Cefprozil of formula (I) igh purity, substantially free of impurities, which comprises preparation of mixed acid anhydride by selecting the sequence and temperature of addition of the reagents and its subsequent condensation with a protected 7-APCA; followed by hydrolysis, isolation and purification to give Cefprozil of formula (I) in the form of a monohydrate.

  一种制备高纯度、基本无杂质的7-[D-α-氨基-α-(4-羟基苯基)乙酰氨基]-3-(1-丙烯-1-基)-3-头孢烷-4-羧酸（即Cefprozil）的方法，包括通过选择试剂的加入顺序和温度来制备混合酸酐，并将其与保护的7-APCA缩合；随后进行水解、分离和纯化，得到以单水合物形式存在的化合物Cefprozil。
• Process for preparation of 7-[a-amino (4-hydroxyphenyl) acetamido]-3-substituted-3-cephem-4-carboxylic acid
  申请人：Tyagi Dutt Om

  公开号：US20060149096A1

  公开（公告）日：2006-07-06

  A process for preparation of 7-[D-α-amino-α-(4-hydroxyphenyl)acetamido]-3-(1-propen-1-yl)-3-cepham-4-carboxylic acid viz. Cefprozil of formula (I) igh purity, substantially free of impurities, which comprises preparation of mixed acid anhydride by selecting the sequence and temperature of addition of the reagents and its subsequent condensation with a protected 7-APCA; followed by hydrolysis, isolation and purification to give Cefprozil of formula (I) in the form of a monohydrate.

  一种制备高纯度、基本无杂质的7-[D-α-氨基-α-(4-羟基苯基)乙酰氨基]-3-(1-丙烯-1-基)-3-头孢-4-羧酸（式(I)）的方法，包括通过选择试剂的加入顺序和温度制备混合酸酐，然后与保护的7-APCA缩合；随后进行水解、分离和纯化，得到一水合物形式的式(I)的Cefprozil。
• Process for the preparation of 6- D-alpha-amino-(p-hydroxyphenyl)-acetamido penicillanic acid
  申请人：GIST-BROCADES N.V.

  公开号：EP0001133A1

  公开（公告）日：1979-03-21

  Process for the preparation of / D-a-amino-p- hydrox- yphenylacetamido/ groups containing penicillanic acid and cephalosporanic acid derivatives, comprising the acylation of a compounds of the formulae: and/or or and/or wherein R1, R2, and R3 represent the same or a different group and may be selected from a lower alkyl, benzyl, cycloalkyl or phenyl-group and preferably lower alkyl and more preferably a methyl group and wherein X represents a residue selected from the group consisting of hydrogen, acetoxy or a fivemembered heterocyclic thio residue, containing heteroatoms selected from nitrogen, oxygen and/or sulphur and optionally substituted by lower alkyl and wherein an eventually present -NH- radical has optionally been silylated, which compound is previously prepared by the reaction of -6-aminopenicillanic acid or 7-aminocephalosporanic acid or its 3-methyl modifications with at least one equivalent and preferably about 2 with respect to 6-APA, 7-ACA or 7-ADCA and about 3 equivalents with respect to other 3-methyl modifications of 7-ACA of a tri(lower)alkyl silyl groups supplying agent in a dry inert, water insoluble solvent, such as methylene chloride, by rapid mixing of a pre-cooled solution of the compound of formula I-IV with a pre-cooled reaction mixture of at least an equimolar amount of a compound of the formula wherein R4 represents lower alkyl and preferably methyl, R5 represents hydrogen or lower alkyl and preferably methyl, R6 represents lower alkoxy and preferably methoxy and R7 represents lower alkoxy and preferably methoxy, previously prepared from the corresponding Dane salt and an acid chloride under anhydrous conditions in the presence of a tertiary amine as catalyst, such as N-methylmorpholine in a dry, inert, water insoluble, organo solvent such as methylene chloride mixed with a cosolvent or methyl isobutylketone or tetrahydrofuran optionally mixed with a cosolvent, and the continuation of the reactior at a temperature of -10°C or lower and preferably from 2°C to 30°C whereafter the desired compound is recovered by usual methods.

  制备含有青霉素和头孢菌素衍生物的/ D-a-氨基-对羟基-苯基乙酰胺/基团的工艺，包括式中化合物的酰化： 和/或 或 和/或 其中 R1、R2 和 R3 代表相同或不同的基团，可选自低级烷基、苄基、环烷基或苯基，优选低级烷基，更优选甲基，其中 X 代表选自氢、乙酰氧基或五元杂环硫基残基组成的组的残基，五元杂环硫基残基含有选自氮、氧和/或硫的杂原子，可选择被低级烷基取代，其中最终存在的-NH-基可选择被硅烷化、该化合物的制备方法是：将 6-氨基青霉烷酸或 7-氨基头孢烷酸或其 3-甲基修饰物与至少一个当量，就 6-APA、7-ACA 或 7-ADCA 而言最好是约 2 个当量，就 7-ACA 的其他 3-甲基修饰物而言最好是约 3 个当量的三(低级)烷基硅烷基供给剂在干燥的惰性不溶于水的溶剂中反应、将式 I-IV 化合物的预冷溶液与至少等摩尔量的式 I-IV 化合物的预冷反应混合物快速混合，制得三(低级)烷基硅烷基团供给剂的约 3 个当量的 7-ACA 其中 R4 代表低级烷基，最好是甲基；R5 代表氢或低级烷基，最好是甲基；R6 代表低级烷氧基，最好是甲氧基；R7 代表低级烷氧基，最好是甲氧基、在干燥、惰性、不溶于水的有机溶剂如二氯甲烷与助溶剂或甲基异丁基酮或四氢呋喃（任选与助溶剂混合）中，如 N-甲基吗啉，在-10℃或更低温度下，最好在 2℃至 30℃下继续反应，然后用通常的方法回收所需的化合物。
• Salts of amino-beta-lactamic acids and process for the preparation thereof
  申请人：GEMA S.A.

  公开号：EP0127541A2

  公开（公告）日：1984-12-05

  Amino-beta-lactamic acid salts, having the formula: wherein: (X-Y) may form a system having from 1 to 3 carbon atoms, with or without double bond, a) closed, in which: X is an atom selected from among carbon, oxygen, nitrogen and sulphur; Y is methylene; Z is a carboxy, sulphonic or phosphonic group. b) open, which may comprise a double bond, in which: X is an atom of hydrogen or a methyl, hydroxymethyl or thiol group, Y is an acid radical chosen from the group formed by sulphonic, phosphonic and sulphoamidic acid; Z is missing. R is an atom or hydrogen, or a methoxyl or ethoxyl group. R is, when present, methyl, acetoxymethyl, acylthiomethyl, such as acetyl and benzoyl derivatives, methoxy, chlorine, carbamoyloxymethyl, azido, azidomethyl (alpha, beta)-thioethylamine or a thiomethyl-heterocyclic derivative of the thiazole, thiadiazole, triazole, tetrazole, oxazole, oxadiazole, pyrimidine and imidazole nuclei. R2 is an atom of hydrogen or a methyl, ethyl, benzyl or aryl group. m, n may be the same or different and may range from 1 to 4, forming a ring or m = n = 0 to form an open chain. A process for their preparation is also disclosed.

  具有以下式子的氨基-beta-乳酸盐 其中(X-Y)可构成一个具有 1 至 3 个碳原子的体系，具有或不具有双键，a) 封闭，其中：a) 封闭式，其中：X 是选自碳、氧、氮和硫的原子；Y 是亚甲基；Z 是羧基、磺酸基或膦酸基：X 是氢原子或甲基、羟甲基或硫醇基；Y 是酸基，选自磺酸、膦酸和磺酰胺酸组成的基团；Z 缺失。R 是原子或氢、甲氧基或乙氧基。R 是甲基、乙酰氧甲基、酰硫基甲基（如乙酰基和苯甲酰衍生物）、甲氧基、氯、氨基甲酰氧甲基、叠氮、叠氮甲基（α，β）-硫代乙胺或噻唑、噻二唑、三唑、四唑、噁唑、噁二唑、嘧啶和咪唑核的硫代甲基三环衍生物。m、n 可以相同或不同，范围从 1 到 4，形成一个环或 m = n = 0 形成一个开放链。此外，还公开了其制备工艺。
• Intermediates in cephalosporin production
  申请人：——

  公开号：US20040192909A1

  公开（公告）日：2004-09-30

  A salt of PACA with an amidine and its use in the production of cefprozil.

  一种含脒的 PACA 盐及其在头孢丙烯生产中的应用。