N-benzyloxycarbonylamino-3-(4-methoxyphenyl)propionic acid ethyl ester | 115424-04-9

• 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: N-benzyloxycarbonylamino-3-(4-methoxyphenyl)propionic acid ethyl ester
• 英文别名: ethyl (2S)-3-(4-methoxyphenyl)-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 115424-04-9
• 化学式: C₂₀H₂₃NO₅
• 分子量: 357.406
• InChiKey: NTXSALYLWCCBIE-SFHVURJKSA-N

物化性质

• 沸点：
  519.3±50.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonylamino-3-(4-methoxyphenyl)propionic acid ethyl ester 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 7.0h， 以86%的产率得到(S)-benzyl (1-hydroxy-3-(4-methoxyphenyl)propan-2-yl)carbamate
  参考文献：
  名称：

  A Simple and Efficient Procedure for the Synthesis of Optically Active 4-Methoxy-α-Methylphenylethylamine from Tyrosine

  摘要：

  Optically active 4-methoxy-alpha-methylphenylethylamine (1), a useful chiral building block in medicinal chemistry, was synthesized from L- or D-tyrosine by using a simple and efficient procedure via one-pot zinc reduction of the corresponding O-tosylate (4) in the presence of H2O and NaI in pure form.

  DOI：

  10.1080/00397919808007167
• 作为产物：
  描述：

  4-甲氧基-L-苯丙氨酸 在 氯化亚砜 、 potassium carbonate 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 0.5h， 生成 N-benzyloxycarbonylamino-3-(4-methoxyphenyl)propionic acid ethyl ester
  参考文献：
  名称：

  Asymmetric Synthesis of Unnatural Amino Acids and Tamsulosin Chiral Intermediate

  摘要：

  An efficient and enantioselective hydrogenation of N-acetylamino phenyl acrylic acids was successfully developed by using ruthenium catalyst. This methodology is important in the field of pharmaceuticals and provides a new process for the preparation of unnatural amino acids and tamsulosin chiral intermediate. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource: Full experimental and spectral details.]

  DOI：

  10.1080/00397911.2012.748075

文献信息

• Process for preparation of tamsulosin and its aralkylamine derivatives
  申请人：Jih Hwu Ru

  公开号：US20070015939A1

  公开（公告）日：2007-01-18

  The present invention discloses a new process for the synthesis of tamsulosin and its aralkylamine derivatives, especially (R)-(−)-5-2-[2-(2-alkoxyphenoxy)ethylamino]propyl}-2-alkoxybenzenesulfonamides having the following formula 1 (where R 1 and R 2 represent C 1 -C 4 alkyl groups) and their hydrochloride thereof, and other various pharmaceutical used salts. Tamsulosin hydrochloride (R 1 =Et, R 2 =Me, in its hydrochloride salt form) is an antagonist of α-A adrenoceptors in the prostate. Tamsulosin•HCl occurs as white crystals, which melt with decomposition at approximately 230° C. It is sparingly soluble in water and in methanol, slightly soluble in glacial acetic acid and in ethanol, and practically insoluble in ether.

  本发明公开了一种合成坦洛新及其芳基胺衍生物的新工艺，特别是具有以下化学式1的(R)-(−)-5-2-[2-(2-烷氧基苯氧基)乙基氨基]丙基}-2-烷氧基苯磺酰胺（其中R1和R2代表C1-C4烷基基团）及其盐酸盐，以及其他各种药用盐。坦洛新盐酸盐（R1=Et，R2=Me，在其盐酸盐形式中）是前列腺α-A肾上腺素受体的拮抗剂。坦洛新•HCl呈白色晶体，约在230°C左右分解熔化。它在水和甲醇中溶解度较低，在冰乙酸和乙醇中稍溶，在醚中几乎不溶。
• US7282606B2
  申请人：——

  公开号：US7282606B2

  公开（公告）日：2007-10-16
• Asymmetric Synthesis of Unnatural Amino Acids and Tamsulosin Chiral Intermediate
  作者：Veera Reddy Arava、Srinivasulu Reddy Amasa、Bharat Kumar Goud Bhatthula、Laxmi Srinivas Kompella、Venkata Prasad Matta、M. C. S. Subha

  DOI：10.1080/00397911.2012.748075

  日期：2013.11.2

  An efficient and enantioselective hydrogenation of N-acetylamino phenyl acrylic acids was successfully developed by using ruthenium catalyst. This methodology is important in the field of pharmaceuticals and provides a new process for the preparation of unnatural amino acids and tamsulosin chiral intermediate. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource: Full experimental and spectral details.]
• A Simple and Efficient Procedure for the Synthesis of Optically Active 4-Methoxy-α-Methylphenylethylamine from Tyrosine
  作者：Harumichi Kohno、Takeo Iwakuma a)、Koichiro Yamada

  DOI：10.1080/00397919808007167

  日期：1998.6

  Optically active 4-methoxy-alpha-methylphenylethylamine (1), a useful chiral building block in medicinal chemistry, was synthesized from L- or D-tyrosine by using a simple and efficient procedure via one-pot zinc reduction of the corresponding O-tosylate (4) in the presence of H2O and NaI in pure form.