(Z)-2-(2-amino-4-thiazolyl)-2-[[1-(t-butoxycarbonyl)-1-methylethoxy]imino]-acetic acid 2-benzthiazolyl thioester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: (Z)-2-(2-amino-4-thiazolyl)-2-[[1-(t-butoxycarbonyl)-1-methylethoxy]imino]-acetic acid 2-benzthiazolyl thioester
• 英文别名: (Z)-2-(2-amino-4-thiazolyl)-2-[[1-(t-butoxycarbonyl)-1-methylethoxy]imino]-acetic acid 2-benzthiazolyl-thioester；2-(2-amino-4-thiazolyl)-2-[[(Z)-1-(t-butoxycarbonyl)-1-methylethoxy]imino]-acetic acid 2-benzthiazolyl thioester；tert-butyl 2-[(Z)-[1-(2-amino-1,3-thiazol-4-yl)-2-(1,3-benzothiazol-2-ylsulfanyloxy)-2-oxoethylidene]amino]oxy-2-methylpropanoate
• 化学式: C₂₀H₂₂N₄O₅S₃
• 分子量: 494.616
• InChiKey: PPUJXLBJSDOZSM-OYKKKHCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  208
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (3S,4S)-3-amino-4-carbamoyloxymethyl-2-oxo-1-azetidine-sulfonic acid sodium 、 (Z)-2-(2-amino-4-thiazolyl)-2-[[1-(t-butoxycarbonyl)-1-methylethoxy]imino]-acetic acid 2-benzthiazolyl thioester 在 丙酮 、 水 作用下， 以 acetone - water 为溶剂， 反应 15.0h， 以After lyophilization (3S,4S)-3-[(2-amino-4-thiazolyl)-2-(Z)-[[1-(t-butoxycarbonyl)-1-methylethoxy]imino]-acetamido]-4-carbamoyloxymethyl-2-oxo-1-azetidinesulfonic acid-sodium salt is obtained的产率得到
  参考文献：
  名称：

  4-carbamoyloxymethyl-1-sulfo-2-oxoazetidine derivatives and their

  摘要：

  式子为##STR1##的化合物在制备4-位置具有羰酰氧甲基的1-磺酸基-2-氧代氮杂环化合物的中间体时很有用。最终产物化合物具有抗微生物和/或β-内酰胺酶抑制活性，并且对于人类和家畜来说是有价值的药物。

  公开号：

  US04673739A1
• 作为产物：
  描述：

  二硫化二苯并噻唑 在 N-甲基吗啉 、 盐酸 、 亚磷酸三乙酯 作用下， 以 甲醇 、 2-(2-amino-4-thiazolyl)-2-[[(Z)-1-(t-butoxycarbonyl)-1-methylethoxy]imino]-acetic acid 、 乙腈 为溶剂， 生成 (Z)-2-(2-amino-4-thiazolyl)-2-[[1-(t-butoxycarbonyl)-1-methylethoxy]imino]-acetic acid 2-benzthiazolyl thioester
  参考文献：
  名称：

  4-Carbamoyloxymethyl-1-sulfo-2-oxoazetidine derivatives and their

  摘要：

  揭示的是一般式为：##STR1##的化合物，其中R.sup.1是氢原子或较低的烷基基团，R.sup.2是氢原子或酯基团，所述衍生物具有(3S,4S)-构型；以及其药学上可接受的盐和酯。这些化合物具有抗微生物和/或β-内酰胺酶抑制活性，并且作为人类和驯养动物的药物具有价值。

  公开号：

  US04572801A1

文献信息

• Process for the manufacture of 1-sulpho-2-oxoazetidine carboxylic acid
  申请人：Hoffmann-La Roche Inc.

  公开号：US04652651A1

  公开（公告）日：1987-03-24

  The manufacture of 1-sulpho-2-oxazetidine derivatives of the formula ##STR1## in which Het is an optionally amino-substituted, 5- or 6-membered, aromatic heterocycle containing 1 or 2 nitrogen atoms and optionally also an oxygen or sulphur atom, R.sup.1 is hydrogen, lower alkyl, phenyl-lower alkyl, lower alkanoyl, lower alkoxycarbonyl, lower alkenyl-lower alkyl, lower alkoxycarbonyl-lower alkyl, phenyl-lower-alkoxycarbonyl-lower alkyl, nitrophenyl-lower-alkoxycarbonyl-lower alkyl or carboxy-lower alkyl and R.sup.2 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, lower alkoxycarbonyl, lower alkanoyloxy-lower alkyl, lower alkoxycarbonyl-lower alkenyl, hydroxyiminomethyl, lower alkoxyiminomethyl, carbamoyl, carbamoyl-lower alkenyl or carbamoyloxy-lower alkyl, the group .dbd.NOR.sup.1 being present at least partially in the syn-form, in racemic form or in the form of the 3S-enantiomer, and of readily hydrolyzable esters and pharmaceutically compatible salts of these compounds, by acylating a compound of the formula ##STR2## in which R.sup.20 equals R.sup.2 or can also represent a 2,2-dimethyl-1,3-dioxolan-4-yl group and R.sup.3 is hydrogen or sulpho, or a salt thereof with a thioester of the formula ##STR3## in which Het is as above and R.sup.10 has any of the values of R.sup.1 except carboxy-lower alkyl, and can also represent a tri-lower alkyl-silyl-lower-alkoxycarbonyl-lower alkyl group or a carboxy-lower alkyl group converted into a readily hydrolyzable ester group, and the group .dbd.NOR.sup.10 is present at least partially in the syn-form, and carrying out subsequent steps (N-sulphonation, conversion of R.sup.20 into R.sup.2, R.sup.10 into R.sup.1), some of which are optional. The invention also provides certain novel products of formula I and benzthiazolyl thioesters of formula III per se and the preparation of the benzthiazolyl thioesters by esterifying corresponding carboxylic acids. Finally, the invention provides a process for the preparation of carboxylic acids in which R.sup.1 is t-alkoxycarbonylmethyl. The compounds of formula I have antimicrobial activity.

  该专利描述了一种制备1-磺酸-2-噁唑环丙烷衍生物的方法，其化学式为##STR1##其中Het是一个含有1或2个氮原子和可能还有一个氧原子或硫原子的可选氨基取代的5或6元芳香杂环，R.sup.1是氢、低烷基、苯基-低烷基、低烷酰、低烷氧羰基、低烯基-低烷基、低烷氧羰基-低烷基、苯基-低烷氧羰基-低烷基、硝基苯基-低烷氧羰基-低烷基或羧基-低烷基，R.sup.2是氢、低烷基、低烯基、低炔基、低烷氧羰基、低烷酰氧基-低烷基、低烷氧羰基-低烯基、羟基亚胺甲基、低烷氧亚胺甲基、氨甲酰基、氨甲酰基-低烯基或氨甲酰氧基-低烷基，.dbd.NOR.sup.1基团至少部分以syn-形式存在，是外消旋形式或3S-对映体形式，以及这些化合物的易水解酯和药用兼容盐的制备方法。
• .beta.-Lactams
  申请人：Hoffman-La Roche Inc.

  公开号：US04576751A1

  公开（公告）日：1986-03-18

  There is presented optically uniform .beta.-lactams of the formulae ##STR1## wherein Z is a readily cleavable acyl group, R.sup.1 is amino or a group convertible into amino, R.sup.2 is hydrogen or a readily cleavable protecting group and R.sup.3 and R.sup.4 each are a lower hydrocarbon group which optionally contains oxygen and which is attached via a carbon atom, whereby these groups can also be joined with one another to form a ring, with the proviso that R.sup.1 is a readily cleavable acylamino when R.sup.2 is hydrogen, and the corresponding optical antipodes, their manufacture and use in the manufacture of antimicrobially-active .beta.-lactams as well as novel intermediates usable in their manufacture.

  提供了光学均匀的β-内酰胺，其结构式如下：其中Z是易于水解的酰基，R.sup.1是氨基或可转化为氨基的基团，R.sup.2是氢或易于水解的保护基团，R.sup.3和R.sup.4分别是低碳氢基团，可选地含氧，并通过碳原子连接，这些基团也可以相互连接形成环，但R.sup.1是易于水解的酰胺基团当R.sup.2为氢时，以及相应的光学对映体，它们的制造和用于制造抗微生物活性的β-内酰胺以及在其制造中可用的新型中间体。
• Process for the preparation of cephalosporins
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0253507B1

  公开（公告）日：1994-03-23
• 1-Sulfo-2-azetidinone derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0093376B2

  公开（公告）日：1999-04-07
• US4572801A
  申请人：——

  公开号：US4572801A

  公开（公告）日：1986-02-25