(2S)-3-amino-2-((1R)-1-hydroxyethyl)propionic acid | 120236-27-3

• 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: (2S)-3-amino-2-((1R)-1-hydroxyethyl)propionic acid
• 英文别名: (2S,3R)-aminomethyl-3-hydroxybutanoic acid；(2S,3R)-2-aminomethyl-3-hydroxybutyric acid；(2S,3R)-2-(aminomethyl)-3-hydroxybutanoic acid
• CAS: 120236-27-3
• 化学式: C₅H₁₁NO₃
• 分子量: 133.147
• InChiKey: WFRNRWHEMQWFRH-DMTCNVIQSA-N

物化性质

• 沸点：
  326.9±32.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S)-3-amino-2-((1R)-1-hydroxyethyl)propionic acid 在 N-t-butyl-2-benzimidazolylsulfenamide 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以89%的产率得到(1'R,3S)-3-<1'-(hydroxy)ethyl>-2-azetidinone
  参考文献：
  名称：

  使用亚磺酰胺/三苯膦从β-氨基酸制备β-内酰胺的简便方法

  摘要：

  通过用N-烷基-2-苯并噻唑基亚磺酰胺和三苯基膦处理，β-，γ-和δ-氨基酸易于高产率地环化为相应的β-，γ-和δ-内酰胺。

  DOI：

  10.1016/0040-4039(95)00658-y
• 作为产物：
  描述：

  (2S,3R)-2-[(苯甲酰基氨基)甲基]-3-羟基丁酸甲酯 在 三乙胺 作用下， 以 12N-hydrochloric acid 、 甲苯 、 乙腈 为溶剂， 以80%的产率得到(2S)-3-amino-2-((1R)-1-hydroxyethyl)propionic acid
  参考文献：
  名称：

  Method of preparing a derivative of optically active azetidin-2-one

  摘要：

  为制备化合物(1'R,3S)-3-(1'-三取代硅氧基乙基)吖啶-2-酮，(2S,3R)-2-氨甲基-3-羟基丁酸与一种来自硫酰氯、氯化氢和对甲苯磺酸组合的至少一种化合物在醇的存在下发生反应，从而获得相应酯的盐。该盐在金属催化剂的存在下与三取代硅烷发生反应，从而保护酯的羟基，然后与碱发生反应，从而获得(2S,3R)-2-氨甲基-3-(三取代硅氧基)丁酸酯。随后，在格氏试剂或金属酰胺的存在下将酯转化为内酰胺，从而获得(1'R,3S)-3-(1'-三取代硅氧基乙基)吖啶-2-酮。该化合物为制备β-内酰胺类抗菌药物如头孢菌素类药物提供了有用的基础。

  公开号：

  US05712388A1

文献信息

• Process for preparing (1'R,3S)-3-(1'-hydroxyethyl)-azetidin-2-one and
  申请人：Takasago International Corporation

  公开号：US05204461A1

  公开（公告）日：1993-04-20

  A process for preparing (1'R,3S)-3-(1'-hydroxyethyl)-azetidin-2-one or a derivative thereof represented by formula (I): ##STR1## wherein R.sup.1 represents a hydrogen atom or a hydroxyl-protective group, is disclosed, comprising reacting (2S,3R)-2-aminomethyl-3-hydroxybutyric acid or a derivative thereof represented by formula (II): ##STR2## wherein R.sup.1 is as defined above, with a sulfenamide represented by formula (III): ##STR3## wherein R.sup.2 represents ##STR4## and R.sup.3 and R.sup.4 each represent a hydrogen atom or a cyclic or acyclic hydrocarbon group, provided that they do not simultaneously represent a hydrogen atom, or R.sup.3 and R.sup.4 are taken together with the adjacent nitrogen atom to form a heterocyclic group, and triphenylphosphine. The reaction yield is high, and the sulfenamide (III) used as a lactamization reagent is cheap and can be recovered after the reaction.

  揭示了一种制备(1'R,3S)-3-(1'-羟乙基)-吖啶-2-酮或其衍生物的方法，其表示为式(I)：其中R.sup.1代表氢原子或羟基保护基，包括将(2S,3R)-2-氨甲基-3-羟基丁酸或其衍生物（II式）与一种代表为式(III)的磺胺酰胺反应，其中R.sup.2代表...和R.sup.3和R.sup.4分别代表氢原子或环状或非环状碳氢基团，前提是它们不同时代表氢原子，或R.sup.3和R.sup.4与相邻的氮原子一起形成杂环基团，以及三苯基膦。 反应产率高，作为内酰胺化试剂使用的磺胺酰胺(III)便宜且可在反应后回收。
• Ruthenium catalyzed process for preparing 4-acetoxyazetidinones
  申请人：Takasago International Corporation

  公开号：US05204460A1

  公开（公告）日：1993-04-20

  A simplified process for preparing 4-acetoxyazetidinones of formula (I): ##STR1## wherein Z is a hydrogen atom, a lower alkyl group or a hydroxyethyl group which may or may not be protected is disclosed. According to the invention, azetidinones of formula (II): ##STR2## wherein Z has the same meaning as defined above and Y is a hydrogen atom or a carboxyl group is reacted with acetic acid and an oxidizing agent in the presence of a ruthenium compound represented by the formula [Ru(B).sub.2 (L)].sub.m wherein B is Cl, Br or l, m is a positive integer, and L is 1,5-cyclooctadiene, norbornadiene, cycloheptatriene, cyclooctatetraene or benzene which may or may not have a lower alkyl group as a substituent, as a catalyst.

  本发明公开了一种制备式（I）的4-乙酰氧基氮杂环丁酮的简化过程：##STR1## 其中Z是氢原子，低级烷基或羟乙基基团，可以或不可以被保护。根据本发明，式（II）的氮杂环丁酮：##STR2## 其中Z具有上述定义的相同含义，Y是氢原子或羧基团，与乙酸和氧化剂在铑化合物的存在下反应，所述铑化合物由式[Ru(B).sub.2 (L)].sub.m表示，其中B为Cl、Br或l，m为正整数，L为1,5-环辛二烯、去氢萘二烯、环庚三烯、环辛四烯或苯，可以或不可以有低级烷基基团作为取代基，作为催化剂。
• Process for the manufacture of 4-acyloxy-3-hydroxyethyl-azetidinones
  申请人：Ciba-Geigy Corporation

  公开号：US05274188A1

  公开（公告）日：1993-12-28

  The invention relates to a novel process for the manufacture of (3R,1'R)-4-acyloxy-3-(1'-hydroxyethyl)-2-azetidinones of formula ##STR1## in which R.sup.1 represents lower alkyl or aryl, by enantioselective reduction of the carbonyl group in a suitable .alpha.-acylaminomethyl-acetoacetic acid ester, cyclisation of the resulting .alpha.-acylaminomethyl-.beta.-hydroxybutyric acid ester to a 5,6-dihydro-1,3,4H-oxazine with inversion of the carbon atom carrying the hydroxy group, equilibration to form the preferred trans-substituted dihydrooxazine, recleaving to form the configuratively uniform .alpha.-aminomethyl-.beta.-hydroxybutyric acid, ring-closure to form the .beta.-lactam and oxidative acylation at C(4) of the .beta.-lactam. Compounds of formula I can be used as starting materials for the manufacture of .beta.-lactam antibiotics. The invention relates also to novel intermediates.

  本发明涉及一种新型工艺，用于制造式为##STR1##的(3R,1'R)-4-酰氧基-3-(1'-羟乙基)-2-氮杂环己酮，其中R1代表较低的烷基或芳基，通过对适宜的α-酰氨甲基-乙酰乙酸酯中的羰基基团进行对映选择性还原，将得到的α-酰氨甲基-β-羟基丁酸酯环化成带有羟基的5,6-二氢-1,3,4H-噁嗪，翻转携带羟基的碳原子，平衡形成优选的反式取代二氢噁嗪，再次裂解形成构型一致的α-氨甲基-β-羟基丁酸，环合成β-内酰胺，氧化酰化β-内酰胺的C(4)。式I的化合物可用作β-内酰胺类抗生素的原料。本发明还涉及新型中间体。
• A convenient preparative method for β-lactams from β-amino acids using sulfenamide/triphenylphosphine
  作者：Toshiyuki Murayama、Toyohiko Kobayashi、Takashi Miura

  DOI：10.1016/0040-4039(95)00658-y

  日期：1995.5

  β-, γ-, and δ-Amino acids were easily cyclized in high yields to corresponding β-, γ-, and δ-lactams by treatment with N-alkyl-2-benzothiazolylsulfenamide and triphenylphosphine.

  通过用N-烷基-2-苯并噻唑基亚磺酰胺和三苯基膦处理，β-，γ-和δ-氨基酸易于高产率地环化为相应的β-，γ-和δ-内酰胺。
• Method of preparing a derivative of optically active azetidin-2-one
  申请人：Takasago International Corporation

  公开号：US05712388A1

  公开（公告）日：1998-01-27

  To prepare the compound (1'R,3S)-3-(1'-tri-substituted silyloxyethyl)azetidin-2-one, (2S,3R)-2-aminomethyl-3-hydroxybutyric acid is reacted with an alcohol in the presence of at least one compound chosen from the group consisting of thionyl chloride, hydrogen chloride and p-toluene sulfonic acid, thereby obtaining a salt of the corresponding ester. The salt is reacted with a tri-substituted silane in the presence of a metallic catalyst, thereby protecting the hydroxy group of the ester and then reacted with a base, thereby obtaining an ester of (2S,3R)-2-aminomethyl-3-(tri-substituted silyloxy)butyric acid. Subsequently, the ester is transformed into lactam in the presence of a Grignard reagent or a metal amide, thereby obtaining (1'R,3S)-3-(1'-tri-substituted silyloxyethyl)azetidin-2-one. This compound provides a useful base for preparing .beta.-lactam type antimicrobial agents such as carbapenem type agents.

  为制备化合物(1'R,3S)-3-(1'-三取代硅氧基乙基)吖啶-2-酮，(2S,3R)-2-氨甲基-3-羟基丁酸与一种来自硫酰氯、氯化氢和对甲苯磺酸组合的至少一种化合物在醇的存在下发生反应，从而获得相应酯的盐。该盐在金属催化剂的存在下与三取代硅烷发生反应，从而保护酯的羟基，然后与碱发生反应，从而获得(2S,3R)-2-氨甲基-3-(三取代硅氧基)丁酸酯。随后，在格氏试剂或金属酰胺的存在下将酯转化为内酰胺，从而获得(1'R,3S)-3-(1'-三取代硅氧基乙基)吖啶-2-酮。该化合物为制备β-内酰胺类抗菌药物如头孢菌素类药物提供了有用的基础。