acetyloxy[[(1,1-dimethylethoxy)carbonyl]amino]acetic acid methyl ester | 173306-81-5

• 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: acetyloxy[[(1,1-dimethylethoxy)carbonyl]amino]acetic acid methyl ester
• 英文别名: N-tert-butyloxycarbonyl-α-acetoxyglycine methyl ester；methyl 2-acetoxy-2-(tert-butoxycarbonylamino)acetate；methyl N-Boc-2-acetoxyglycine；methyl 2-acetoxy-2-[((1,1-dimethylethoxy)carbonyl)amino]acetate；methyl 2-acetyloxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate
• CAS: 173306-81-5
• 化学式: C₁₀H₁₇NO₆
• 分子量: 247.248
• InChiKey: NVLYIFJPIVHPGY-UHFFFAOYSA-N

物化性质

• 沸点：
  342.0±32.0 °C(Predicted)
• 密度：
  1.159±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  acetyloxy[[(1,1-dimethylethoxy)carbonyl]amino]acetic acid methyl ester 在 phosphate buffer 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 Boc-L-炔丙基甘氨酸
  参考文献：
  名称：

  Zinc mediated addition of active halides to a glycine cation equivalent: Synthesis of N-Boc-L-propargylglycine

  摘要：

  The reaction of allylic, benzylic and propargylic halides with zinc in the presence of the glycine cation equivalent, methyl N-Boc-2-acetoxyglycine, affords Boc protected amino acid derivatives in high yield. Resolution of methyl N-Boc-propargylglycine with alpha-chymotrypsin affords N-Boc-L-propargylglycine in 99% e.e..

  DOI：

  10.1016/s0040-4039(00)73067-x
• 作为产物：
  描述：

  氨基甲酸叔丁酯 在 吡啶 作用下， 以 四氢呋喃 、 苯 为溶剂， 生成 acetyloxy[[(1,1-dimethylethoxy)carbonyl]amino]acetic acid methyl ester
  参考文献：
  名称：

  Zinc mediated addition of active halides to a glycine cation equivalent: Synthesis of N-Boc-L-propargylglycine

  摘要：

  The reaction of allylic, benzylic and propargylic halides with zinc in the presence of the glycine cation equivalent, methyl N-Boc-2-acetoxyglycine, affords Boc protected amino acid derivatives in high yield. Resolution of methyl N-Boc-propargylglycine with alpha-chymotrypsin affords N-Boc-L-propargylglycine in 99% e.e..

  DOI：

  10.1016/s0040-4039(00)73067-x

文献信息

• Synthesis of a Naturally Occurring Diene-Containing Amino Acid and Its Glutamyl Dipeptide viaN-Acyliminium Ion Chemistry
  作者：Martin Berkheij、Jan Dijkink、Olivier R. P. David、Theo Sonke、Denis R. IJzendoorn、Richard H. Blaauw、Jan H. van Maarseveen、Hans E. Schoemaker、Henk Hiemstra

  DOI：10.1002/ejoc.200701016

  日期：2008.2

  The syntheses of the naturally occurring unusual unsaturated amino acid (S)-2-amino-3-methylene-4-pentenoic acid and the corresponding gamma-glutamyl dipeptide are described. Key steps are an N-acyliminium ion addition using allenyhnethylsilane as nucleophile and an enzymatic resolution mediated by the L-aminopeptidase from Pseudomonas putida.

  描述了天然存在的罕见不饱和氨基酸 (S)-2-amino-3-methylene-4-pentenoic 酸和相应的 γ-谷氨酰二肽的合成。关键步骤是使用丙二烯基乙基硅烷作为亲核试剂的 N-acyliminium 离子加成和由来自恶臭假单胞菌的 L-氨基肽酶介导的酶促拆分。
• Hetero-substituted metalloprotease inhibitors
  申请人：The Procter & Gamble Company

  公开号：US06566381B1

  公开（公告）日：2003-05-20

  Heterocyclic substituted compounds having the general structure: which are inhibitors of metalloproteases and which are effective in treating conditions characterized by excess activity of these enzymes.

  具有一般结构的杂环取代化合物：这些化合物是金属蛋白酶抑制剂，对于治疗由这些酶活性过高所表征的疾病有效。
• Expedient Pyrrolizidine Synthesis by Propargylsilane Addition to<i>N</i>-Acyliminium Ions followed by Gold-Catalyzed α-Allenyl Amide Cyclization
  作者：Arjen C. Breman、Jan Dijkink、Jan H. van Maarseveen、Sape S. Kinderman、Henk Hiemstra

  DOI：10.1021/jo901393y

  日期：2009.8.21

  A reaction sequence, involving the addition of (substituted) propargylsilanes to lactam-derived N-acyliminium ions followed by gold-catalyzed cyclization of the resulting α-allenyl amide, is applied in expedient syntheses of pyrrolizidine alkaloids heliotridine and ent-retronecine in five steps from (S)-malic acid.

  在五个步骤中，将反应顺序（包括将（取代的）炔丙基硅烷添加到内酰胺衍生的N-酰基亚胺离子中，然后用金催化的环化所得的α-烯丙基酰胺）进行吡咯烷核生物碱类四氢吡啶和对-维甲酸的合成来自（S）-苹果酸。
• Synthesis of N-protected-.alpha.-substituted-glycine racemic esters by
  申请人：G.D. Searle & Co.

  公开号：US05508466A1

  公开（公告）日：1996-04-16

  A method is described for synthesis of N-Boc-L-propargylglycine, a key intermediate used in the preparation of high-potency, orally-active renin inhibitors. This method involves reaction of an organic halide with a glycine cation equivalent, such as methyl N-Boc-2-acetoxyglycine, in the presence of zinc dust to give Boc-protected amino acid derivatives in high yield. Typically useful organic halides are allylic, benzylic and propargylic halides. Resolution of methyl N-Boc-propargylglycine with .alpha.-chymotrypsin provides N-Boc-L-propargylglycine in high yield.

  本文描述了一种合成N-Boc-L-丙炔基甘氨酸的方法，这是制备高效、口服活性肾素抑制剂的关键中间体。该方法涉及有机卤化物与甘氨酸阳离子当量（例如甲基N-Boc-2-乙酰氧基甘氨酸）在锌粉存在下反应，高产率地得到Boc保护的氨基酸衍生物。通常有用的有机卤化物是烯丙基、苄基和丙炔基卤化物。用.alpha.-胰蛋白酶分离甲基N-Boc-丙炔基甘氨酸可以高产率地得到N-Boc-L-丙炔基甘氨酸。
• Dihetero-substituted metalloprotease inhibitors
  申请人：The Procter & Gamble Company

  公开号：US20030225074A1

  公开（公告）日：2003-12-04

  Disclosed are compounds which are inhibitors of metalloproteases and which are effective in treating conditions characterized by excess activity of these enzymes. In particular, the compounds have a structure according to the following Formula (I): 1 where J, M, Q, T, W, X, Z, R 1 , R 2 , R 3 , R 4 , R 4′ , R 5 , R 6 , R 6′ , R 7 , m, and n have the meanings described in the specification. This invention also includes optical isomers, diastereomers and enantiomers of the formula above, and pharmaceutically-acceptable salts, biohydrolyzable amides, esters, and imides thereof. Also disclosed are pharmaceutical compositions comprising these compounds, and methods of treating or preventing metalloprotease-related maladies using the compounds or the pharmaceutical compositions.

  本发明涉及一种金属蛋白酶抑制剂化合物，用于治疗由这些酶的过度活性引起的疾病。特别地，该化合物具有以下式(I)的结构：其中J、M、Q、T、W、X、Z、R1、R2、R3、R4、R4'、R5、R6、R6'、R7、m和n在规范中有所描述。本发明还包括该式的光学异构体、对映异构体和对映体，以及其药物可接受的盐、生物可水解的酰胺、酯和亚酰酰胺。还公开了包含这些化合物的药物组合物，以及使用该化合物或药物组合物治疗或预防金属蛋白酶相关疾病的方法。