(3S,4S)-3-benzyloxycarbonylamino-4-carbamoyl-2-azetidinone | 86334-66-9

• 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: (3S,4S)-3-benzyloxycarbonylamino-4-carbamoyl-2-azetidinone
• 英文别名: benzyl (3S,4S)-4-carbamoyl-2-oxo-3-azetidinecarbamate；benzyl N-[(2S,3S)-2-carbamoyl-4-oxoazetidin-3-yl]carbamate
• CAS: 86334-66-9
• 化学式: C₁₂H₁₃N₃O₄
• 分子量: 263.253
• InChiKey: TUZKPMSDCPQBGQ-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  111
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4S)-3-benzyloxycarbonylamino-4-carbamoyl-2-azetidinone 在 Dowex 50 W 、 三氧化硫吡啶 作用下， 以2.01 g的产率得到sodium (3S,4S)-benzyloxycarbonylamino-4-carbamoyl-2-azetidinone-1-sulfonate
  参考文献：
  名称：

  Synthesis of carumonam (AMA-1080) and a related compound starting from (2R,3R)-epoxysuccinic acid.

  摘要：

  在对磺胺氟噻嗪进行化学改造的过程中，合成了几种4-氨甲酰-2-氮杂环丁酮-1-磺酸衍生物，旨在提高其抗菌活性。在这些化合物中，(3S, 4S)-3-[2-(2-氨噻唑-4-基)-(Z)-2-(1-羧基-1-甲基乙氧亚胺)乙酰氨基]-4-氨甲酰-2-氮杂环丁酮-1-磺酸(2)被发现对抗革兰氏阴性细菌具有强大的抗菌活性，结果与卡鲁莫南(1, AMA-1080; Ro 17-2301)相当。基于(2R, 3R)-环氧琥珀酸(5)这一易于获取的发酵产物，开发了高效的合成路径，以大规模制备1和2。

  DOI：

  10.1248/cpb.33.3798
• 作为产物：
  描述：

  benzyl (3S,4S)-cis-4-cyano-2-oxo-3-azetidinecarbamate 在 sodium hydroxide 、 双氧水 作用下， 以 二甲基亚砜 、 乙酸乙酯 为溶剂， 生成 (3S,4S)-3-benzyloxycarbonylamino-4-carbamoyl-2-azetidinone
  参考文献：
  名称：

  Antimicrobial 2-oxo-1-azetidinesulphonic acids

  摘要：

  公式为##STR1##的抗微生物2-氧代-1-氮杂环丙磺酸，其中H.sub.2 N ##STR2##代表氨基取代的噻唑基团，R.sup.1是被氨甲酰基、低烷基磺酰基、叠氮基、哌啶基甲酰基、(六氢-1H-氮杂环庚烯-1-基)甲酰基或低烷基炔基取代的低烷基，R.sup.2是氢或低有机基，通常为氨甲酰氧甲基。

  公开号：

  US04816582A1

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。
• 4-Cyano-2-azetidinones and production thereof
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0083039A1

  公开（公告）日：1983-07-06

  4-Cyano-2-azetidinone derivatives represented by the formula wherein R' is an amino group which may be acylated or protected, X is a hydrogen atom or a methoxy group and W is a hydrogen atom or a sulfo group, and methods of producing the same, for example, as represented by and wherein R2 is an acylated or protected amino group, Y is a halogen atom or a group having the formula -OCOR3, -SCOR3 or -S(O)n-R3 (R3 being a hydrocarbyl group and n an integer 1 or 2), R4 is an amino group which may be acylated or protected and X is as defined above. Compounds [I] are useful as advantageous intermediates for the synthesis of optically active 4-substituted-2-azetidinone derivatives, and, when W = S03H, [I] are also useful as antimicrobial agents and as beta-lactamase inhibitors.

  4-氰基-2-氮杂环丁酮衍生物，其式如下 式中 R'为可酰化或保护的氨基，X为氢原子或甲氧基，W为氢原子或磺基，以及生产这些衍生物的方法，例如由以下式子表示的方法 和 其中 R2 是酰化或保护的氨基，Y 是卤素原子或具有式 -OCOR3、-SCOR3 或 -S(O)n-R3 的基团（R3 是烃基，n 是 1 或 2 的整数），R4 是可酰化或保护的氨基，X 如上定义。化合物[I]是合成具有光学活性的 4-取代-2-氮杂环丁酮衍生物的有利中间体，当 W = S03H 时，[I]还可用作抗菌剂和β-内酰胺酶抑制剂。
• OCHIAI, MICHIHIKO;KISHIMOTO, SHOJI;MATSUO, TAISUKE
  作者：OCHIAI, MICHIHIKO、KISHIMOTO, SHOJI、MATSUO, TAISUKE

  DOI：——

  日期：——
• FURLENMEIER, A.;HOFHEINZ, W.;HUBSCHWERLEN, C. N.;ISENRING, H. P.
  作者：FURLENMEIER, A.、HOFHEINZ, W.、HUBSCHWERLEN, C. N.、ISENRING, H. P.

  DOI：——

  日期：——
• US4560508A
  申请人：——

  公开号：US4560508A

  公开（公告）日：1985-12-24