sodium-D-N-(2-methoxycarbonyl-1-methyl-vinyl)-α-amino-(p-hydroxy-phenyl)-acetate | 30650-47-6

• 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
• 英文名称: sodium-D-N-(2-methoxycarbonyl-1-methyl-vinyl)-α-amino-(p-hydroxy-phenyl)-acetate
• 英文别名: sodium D-N-(2-methoxycarbonyl-1-methylvinyl)-α-amino-α-(4-hydroxyphenyl)acetate；sodium N-(2-methoxycarbonyl-1-methylvinyl)-D-2-amino-2-(4-hydroxyphenyl)acetate；sodium N-(2-methoxycarbonyl-1-methylvinyl)-D-α-amino-p-hydroxyphenylacetate；sodium N-(1-methyl-2-methoxycarbonylvinyl)-D-2-amino-2-(4-hydroxyphenyl)acetate；Benzeneacetic acid, 4-hydroxy-alpha-((3-methoxy-1-methyl-3-oxo-1-propenyl)amino)-, monosodium salt；sodium;2-(4-hydroxyphenyl)-2-[[(E)-4-methoxy-4-oxobut-2-en-2-yl]amino]acetate
• CAS: 30650-47-6
• 化学式: C₁₃H₁₄NO₅*Na
• 分子量: 287.248
• InChiKey: GOKJACUSSDJUBD-USRGLUTNSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -3.15
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  98.7
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  sodium-D-N-(2-methoxycarbonyl-1-methyl-vinyl)-α-amino-(p-hydroxy-phenyl)-acetate 、 6'-amino-penicillanoyloxymethyl penicillanate 1,1-dioxide 生成 6'-(2-Amino-2-[4-hydroxyphenyl]acetamido)penicillanoyloxymethyl Penicillanate 1,1-Dioxide
  参考文献：
  名称：

  Bis-esters of methanediol with penicillins and penicillanic acid

  摘要：

  6'-酰胺基青霉烷酸氧甲基酯是一种有用的抗菌剂。6'-氨基青霉烷酸氧甲基酯、卤代甲基酯、烷基磺酰氧甲基酯和芳基磺酰氧甲基酯是上述抗菌剂的有用中间体。

  公开号：

  US04244951A1
• 作为产物：
  描述：

  N-(4-羟苯基)甘氨酸 在 sodium hydroxide 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 sodium-D-N-(2-methoxycarbonyl-1-methyl-vinyl)-α-amino-(p-hydroxy-phenyl)-acetate
  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

• Production of p-hydroxycephalexin
  申请人：Bristol-Myers Company

  公开号：US03985741A1

  公开（公告）日：1976-10-12

  Improved yields of 7-[D-.alpha.-amino-.alpha.-(4-hydroxy- and 3-chloro-4-hydroxy-phenyl)acetamido]-3-methyl-3-cephem-4-carboxylic acids are obtained by acylating 7-aminodesacetoxycephalosporanic acid with the mixed anhydride (from ethyl chloroformate) of the ring-substituted 2-phenylglycine when the latter's .alpha.-amino group has been blocked by reaction with a .beta.-keto compound such as methyl acetoacetate. Improved purification processes include the use of dimethylformamide and acetonitrile solvates and solvates and bis-anthraquinone-1,5-disulfonic acid salts.

  通过使用环取代的2-苯基甘氨酸的混合酸酐（来自氯甲酸乙酯）对7-氨基脱乙酰头孢烯酸进行酰化，可以获得7-[D-.alpha.-氨基-.alpha.-(4-羟基和3-氯-4-羟基-苯基)乙酰氨基]-3-甲基-3-头孢烷-4-羧酸的产率提高。当后者的α-氨基团经过与β-酮类化合物（如乙酰乙酸甲酯）反应后被阻断时。改进的纯化过程包括使用二甲基甲酰胺和乙腈溶剂和溶剂和双蒽醌-1,5-二磺酸盐。
• 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。
• Process for the preparation of a (D-alpha-amino-(p-hydroxyphenyl)-acetamido) group containing cephalosporanic acid derivatives
  申请人：GIST-BROCADES N.V.

  公开号：EP0019345A1

  公开（公告）日：1980-11-26

  Process for the preparation of [D-a-amino-(p- hydroxyphenyl)acetamido] groups containing cephalosporanic acid derivatives, comprising the acylation of a compound of the formulae: wherein R,, R2 and R3 representthe 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 an wherein X represents a residue selected from the group consisting of hydrogen, acetoxy or a five-membered 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 7-aminocephalosporanic acid or its 3-methyl modifications with at least one equivalent and preferably about two 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 offormulae I and Il with a pre-cooled reaction mixture of at least an equimolecular 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, organic solvent such as methylene chloride mixed with a co-solvent or methyl isobutylketone or tetrahydrofuran optionally mixed with a co-solvent, and the continuation of the reaction at a temperature of -10°C or lower and preferably from -20°C to -30°C whereafter the desired compound is recovered by usual methods.

  制备含有头孢菌素衍生物的[D-a-氨基-(对羟基苯基)乙酰氨基]基团的工艺，包括将式中的化合物酰化： 其中 R、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。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，该残基含有选自氮、氧和/或硫的杂原子，并任选被低级烷基取代，其中最终存在的-NH-基任选被硅烷化、该化合物的制备方法是：在干燥、惰性、不溶于水的溶剂（如二氯甲烷）中，将 7-氨基头孢烷酸或其 3-甲基修饰物与至少一个当量，最好是约两个当量的 7-ACA 的其他 3-甲基修饰物的三(低级)烷基硅烷基团供给剂反应，将式 I 和 Il 所示化合物的预冷溶液与至少等分子量的式化合物的预冷反应混合物迅速混合 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、 和 R7 代表低级烷氧基，最好是甲氧基，以前是在无水条件下，以叔胺为催化剂，如 N-甲基吗啉为催化剂，在干燥、惰性、不溶于水的有机溶剂如二氯甲烷中，从相应的 Dane 盐和酰氯中制备的、在干燥、惰性、不溶于水的有机溶剂如二氯甲烷与助溶剂混合，或甲基异丁基酮或四氢呋喃与助溶剂混合的情况下，在-10℃或更低的温度下，最好在-20℃至-30℃的温度下继续反应，然后用通常的方法回收所需的化合物。
• Improvements in or relating to deesterification to acids
  申请人：ELI LILLY AND COMPANY

  公开号：EP0132987B1

  公开（公告）日：1987-09-16
• PHENYL-GLYCINE DERIVATIVES
  申请人：CHINOIN Gyogyszer és Vegyészeti Termékek Gyára RT.

  公开号：EP0437566B1

  公开（公告）日：1994-09-28